Dibenzylamine → N,N-dibenzyl-2-benzyloxy-4-formylbenzamide

HRID 1583039Notes

Reaction equation

HRID 1583039 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([CH:18]=[O:19])[CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:20]([NH:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C1(N(C)C(=O)C2C=C(C=O)C=CC=2OCC2C=CC=CC=2)C=CC=CC=1>>[CH2:28]([N:27]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:11](=[O:13])[C:10]1[CH:14]=[CH:15][C:16]([CH:18]=[O:19])=[CH:17][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 3

HCID 7656DibenzylamineHCID 22716821N-phenyl-N-methyl-2-benzyloxy-5-formylbenzamideHCID 227168252-Benzyloxy-4-formylbenzoic acid

Product 1

HCID 22716781N,N-dibenzyl-2-benzyloxy-4-formylbenzamide

Procedure

N,N-dibenzyl-2-benzyloxy-4-formylbenzamide was prepared from 2-benzyloxy-4-formylbenzoic acid (146 mg, 1 eq) and dibenzylamine (0.22 mL, 2 eq) using the same procedure as for N-phenyl-N-methyl-2-benzyloxy-5-formylbenzamide. The product was obtained as a brown oil (236 g, 95%). 1H NMR (CDCl3) δ9.96 (s, 1H, O═C—H), 5.24 (m, 3H, OCH2Ph and NCH2Ph), 4.33 (d, 1H, NCH2Ph), 4.11 (m, 2H, NCH2Ph).

Sources & evidence

ORD record
ord-12f6a936adef4cbda6fb689ee7095368
Source dataset
uspto-grants-2004_05
Patent number
US06740670B2

Reaction notes

Loading…