Benzylamine → HCID 11221282, compound

HRID 2106174Notes

Reaction equation

HRID 2106174 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]2[N:14]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:15]=[C:16]([C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=3)[C:10]=2[CH2:9]1)=O)(C)(C)C.C(OC(N1CCC(=O)CC1)=O)(C)(C)C.C(N)C1C=CC=CC=1.[N+](C1C=CC(C=C[N+]([O-])=O)=CC=1)([O-])=O>C1(C)C=CC=CC=1>[CH2:26]([N:14]1[C:11]2[CH2:12][CH2:13][NH:8][CH2:9][C:10]=2[C:16]([C:17]2[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=2)=[CH:15]1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 1378423156-41-0HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 15965885HCID 15965885, compound

Product 1

HCID 11221282HCID 11221282, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

1-Benzyl-3-(4-nitro-phenyl)-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester. To a stirred solution of 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (0.69 g) in toluene (5 mL) was added 378 μL of benzylamine. The mixture was stirred for 10 min and then 0.70 g of silica gel (SiO2) was added. After stirring at RT for 8 h, 0.77 g of 1-nitro-4-(2-nitro-vinyl)-benzene in toluene (5 mL) was added and the mixture was stirred for 14 h at RT. The mixture was then filtered through diatomaceous earth and the filtrate was concentrated in vacuo. Chromatography on SiO2 (8 to 20% EtOAc/hexanes) afforded 0.48 g of the desired compound. MS (ESI): exact mass calculated for C25H27N3O4, 433.20; found, m/z 434.2 [M+H]+, 456.2 [M+Na]+.

Workup

  1. addition0.70 g of silica gel (SiO2) was added
  2. stirringAfter stirring at RT for 8 h
  3. stirringthe mixture was stirred for 14 h at RT
  4. filtrationThe mixture was then filtered through diatomaceous earth
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-984e8d3ff53f447195d3e152956cbc77
Source dataset
uspto-grants-2009_08
Patent number
US07579470B2

Reaction notes

Loading…