Benzylamine → 1-Benzyl-3-(5-methyl-thiophen-2-yl)-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine

HRID 2106200Notes

Reaction equation

HRID 2106200 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]2[N:14]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:15]=[C:16]([C:17]3[S:18][C:19]([CH3:22])=[CH:20][CH:21]=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.CC1SC(C=C[N+]([O-])=O)=CC=1>C1(C)C=CC=CC=1>[CH2:23]([N:14]1[C:11]2[CH2:12][CH2:13][NH:8][CH2:9][C:10]=2[C:16]([C:17]2[S:18][C:19]([CH3:22])=[CH:20][CH:21]=2)=[CH:15]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 539158762-Methyl-5-(2-nitro-vinyl)-thiopheneHCID 672694411-Benzyl-3-(5-methyl-thiophen-2-yl)-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester

Product 1

HCID 597526601-Benzyl-3-(5-methyl-thiophen-2-yl)-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-Benzyl-3-(5-methyl-thiophen-2-yl)-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester. A mixture of 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (0.54 g) and 300 μL of benzylamine in toluene (10 mL) was heated at reflux for 6 h using a Dean-Stark apparatus. The solution was cooled to RT and 0.47 g of 2-methyl-5-(2-nitro-vinyl)-thiophene was added. The mixture was stirred for 16 h at RT and then was concentrated in vacuo. The residue was chromatographed on SiO2 (1 to 30% EtOAc/hexanes) to afford 281.9 mg of the desired compound. TLC (SiO2, 33% EtOAc/hexanes): Rf=0.54

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 h
  3. concentrationwas concentrated in vacuo
  4. customThe residue was chromatographed on SiO2 (1 to 30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ee28a0784062405b89a0d0b22f49d4b3
Source dataset
uspto-grants-2009_08
Patent number
US07579470B2

Reaction notes

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