Putrescine → N,N'-bis(Aminobutyl)-2-(benzyloxyhexyl)malonamide

HRID 492657Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH2:6].[CH2:7]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]([C:27]([O:29]CC)=O)[C:22]([O:24]CC)=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>>[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:27](=[O:29])[CH:21]([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][O:14][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:22]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][NH2:6])=[O:24]

Participants

Reactant 2

HCID 1045Putrescine

HCID 10383239Diethyl 2-(benzyloxyhexyl)malonate

Product 1

HCID 59301959N,N'-bis(Aminobutyl)-2-(benzyloxyhexyl)malonamide

Conditions

Temperature: 90 °C

Procedure

To a large excess of 1,4-diaminobutane (85 g, 0.964 mol) at 90° C. under argon was slowly added (over 2 hours) B2 (10.50 g, 0.030 mol). The solution was heated at 90° C. overnight and the excess diamine distilled off under reduced pressure (0.1 mbar, 28° C.) to quantitatively yield the title compound as a pale yellow low melting point solid: C24H42N4O3 requires 434. Found DCl: M+ +1 435. I.R. 1664 cm−1 (CO2). δH (CDCl3) 1.15-1.40 (10H, br m, (CH2)3CH2CH, NH2), 1.40-1.60 (10H, br m, (CH2)2CH2NH2, CH2CH2O), 1.76 (2H, q, CH2CH), 2.63 (4H, t, CH2NH2), 2.93 (2H, t, CH2CH), 3.16 (4H, q, CH2NH), 3.37. (2H, t, CH2OCH2Ph), 4.42 (2H, s, CH2Ph), 7.26 (5H, m, Ph), 7.61 (2H, t, CONH). δC (CDCl3) 25.7 (1C, CH2(CH2)2CH), 26.6 (2C, CH2CH2NH2), 28.8, 29.4 (2C, CH2CH2CH, CH2CH2O), 30.6 (2C, CH2CH2NH), 32.7 (1C, CH2CH), 39.0 (2C, CH2NHCO), 41.4 (2C, CH2NH2), 54.7 (1C, CHCO), 70.1, 72.6 (2C, CH2OCH2), 127.2 (1C, CH(CH)2C), 127.3 (2C, CHC), 128.0 (2C, CHCHC), 138.5 (1C, CCH2O), 171.0 (2C, CONH).

Workup

distillationthe excess diamine distilled off under reduced pressure (0.1 mbar, 28° C.)

Sources & evidence

ORD record: ord-5d19ab4bf1d54f64aaedbb68695322a1
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07531676B2

Reaction notes

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