5-Benzyloxyindole → 5-(Benzyloxy)-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

HRID 726080Notes

Reaction equation

HRID 726080 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:18]1[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]1>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[C:21]1[CH2:22][CH2:23][NH:18][CH2:19][CH:20]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 146245-BenzyloxyindoleHCID 337214-Piperidone

Product 1

HCID 232904625-(Benzyloxy)-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

Procedure

Starting with 5.0 gm (22 mMol) 5-benzyloxyindole and 6.88 gm (45 mMol) 4-piperidone.HCl.H2O, 6.53 gm (97.6%) of 5-benzyloxy-3-[1,2,5,6-tetrahydro-4-pyridinyl]-1H-indole were recovered as a light yellow solid by the procedure described in Preparation I. The material was used in the subsequent step without further purification.

Workup

  1. customHCl.H2O, 6.53 gm (97.6%) of 5-benzyloxy-3-[1,2,5,6-tetrahydro-4-pyridinyl]-1H-indole were recovered as a light yellow solid by the procedure
  2. customdescribed in Preparation I
  3. customThe material was used in the subsequent step without further purification

Sources & evidence

ORD record
ord-4ec9c7a032604034a378292a6bf4047b
Source dataset
uspto-grants-1998_01
Patent number
US05708008

Reaction notes

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