ChemicalBook CAS DataBase List 1-AMINO-3,3-DIETHOXYPROPANE

1-AMINO-3,3-DIETHOXYPROPANE synthesis

7synthesis methods

Product Name:1-AMINO-3,3-DIETHOXYPROPANE
CAS Number:41365-75-7
Molecular formula:C7H17NO2
Molecular Weight:147.22

107833-73-8

41365-75-7

The general procedure for the synthesis of 1-amino-3,3-diethoxypropane from the compound (CAS:107833-73-8) was as follows: 10% Pd/C catalyst (15 mg) was added to a solution of compound 5 (17.7 g, 0.1 mol) in methanol (20 mL), and the reaction was stirred for 12 hr at room temperature and 10 atmospheres of hydrogen atmosphere. After completion of the reaction, the filtrate was filtered through diatomaceous earth and concentrated under reduced pressure to afford compound 6 (14.4 g, 98% yield) as a colorless oil. The product was characterized by 1H NMR (400 MHz, CDCl3): δ = 1.14 (t, 6H, J = 6.8 Hz), 1.29 (br s, 2H), 1.71 (q, 2H, J = 6.4 Hz), 2.73 (t, 2H, J = 6.4 Hz), 3.45 (q, 2H, J = 7.2 Hz), 3.60 (q, 2H, J = 7.2 Hz), 4.53 (t, 1H, J=5.2 Hz). IR (pure sample): 3385,2953,2831,1621,1389 cm-1; mass spectrum (EI): m/z: 147 [M+].

107833-73-8
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41365-75-7
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Yield:41365-75-7 98%

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen in methanol at 20; under 7600.51 Torr; for 12 h;

Steps:

4.4 1-Amino-3,3-diethoxypropane 6

To a solution of 5 (17.7 g, 0.1 mol) in MeOH (20 mL) was added Pd/C (10%, 15 mg) and stirred at rt for 12 h under 10 atmospheres of H₂. The filtrate through Celite was concentrated under reduced pressure to give 6 (14.4 g, 98%) as a colorless oil. ¹H NMR (400 MHz, CDCl₃): δ = 1.14 (t, 6H, J = 6.8 Hz), 1.29 (br s, 2H), 1.71 (q, 2H, J = 6.4 Hz), 2.73 (t, 2H, J = 6.4 Hz), 3.45 (q, 2H, J = 7.2 Hz), 3.60 (q, 2H, J = 7.2 Hz), 4.53 (t, 1H, J = 5.2 Hz). IR (neat): 3385, 2953, 2831, 1621, 1389 cm^-1; MS (EI): m/z: 147 [M⁺]

References:

Hu, Lemeng;Xiong, Fangjun;Chen, Xiaofei;Chen, Wenxue;He, Qiuqin;Chen, Fener [Tetrahedron Asymmetry,2013,vol. 24,# 4,p. 207 - 211]