tert-butyl N-(4-aminobutyl)carbamate → {4-[(1-allyl-1H-benzoimidazol-2-ylmethyl)-amino]-butyl}-carbamic acid tert-butyl ester

HRID 251105Notes

Reaction equation

HRID 251105 reaction equation
[C:1]([O:5][C:6](=[O:13])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])([CH3:4])([CH3:3])[CH3:2].[CH2:14]([N:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]=[C:18]1[CH:26]=O)[CH:15]=[CH2:16]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:13])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:26][C:18]1[N:17]([CH2:14][CH:15]=[CH2:16])[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4351tert-butyl N-(4-aminobutyl)carbamateHCID 9625211-(prop-2-en-1-yl)-1H-1,3-benzodiazole-2-carbaldehyde

Product 1

HCID 67272329{4-[(1-allyl-1H-benzoimidazol-2-ylmethyl)-amino]-butyl}-carbamic acid tert-butyl esterYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using General Procedure B: Reaction of (4-amino-butyl)-carbamic acid tert-butyl ester in CH2Cl2 and 1-allyl-1H-benzimidazole-2-carbaldehyde gave {4-[(1-allyl-1H-benzoimidazol-2-ylmethyl)-amino]-butyl}-carbamic acid tert-butyl ester as a colorless oil (0.10 g, 30%). 1H NMR (CDCl3) 1.43 (s, 9H), 1.54 (s, 4H), 2.71 (m, 2H), 3.11 (m, 2H), 4.04 (s, 2H), 4.87 (d, 2H, J=5.3 Hz), 5.02 (d, 1H, J=17.1 Hz), 5.19 (d, 1H, J=11.0 Hz), 5.98 (m, 1H), 7.30 (m, 3H), 7.73 (m, 1H)

Sources & evidence

ORD record
ord-56545c69d3c54f129af85ece4e64287a
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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