3-(4-Piperidinyl)-1H-indole → HCID 131720346, compound

HRID 1938357Notes

Reaction equation

HRID 1938357 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[NH:8][CH:7]=1.[NH:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:18]1.C(N1CCC(=O)CC1)(OC(C)(C)C)=O>>[ClH:1].[CH3:16][O:15][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:5][CH2:4][CH2:3][CH2:2][N:29]1[CH2:30][CH2:31][CH:26]([C:19]2[C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[NH:17][CH:18]=2)[CH2:27][CH2:28]1

Participants

4

Reactant 3

HCID 7022353-(4-Piperidinyl)-1H-indoleHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 15068084HCID 15068084, compound

Product 1

HCID 131720346HCID 131720346, compound

Procedure

1.2 g of 3-(4-chlorobutyl)-5-methoxyindole [obtainable by reaction of 5-methoxyindole with 4-chlorobutyryl chloride to give 3-(4-chlorobutyryl)-5-methoxyindole and subsequent reduction with diborane] and 1.0 g of 4-(indol-3-yl)piperidine [obtainable by reaction of N-BOC-4-piperidone with indole, subsequent dehydration and hydrogenation of the resulting double bond, and removal of the protective group] are dissolved in 200 ml of acetonitrile and the mixture is stirred at room temperature for 8 hours. Working-up in a conventional manner gives 3-[1-(4-(5-methoxyindol-3-yl)-butyl)-4-piperidyl]indole, hydrochloride, m.p. 138°-141° (dec.).

Workup

  1. customwith indole, subsequent dehydration and hydrogenation of the resulting double bond, and removal of the protective group]
  2. dissolutionare dissolved in 200 ml of acetonitrile

Sources & evidence

ORD record
ord-6bc66ee4a5cc4a989c63ad7454582cb1
Source dataset
uspto-grants-1997_12
Patent number
US05693655

Reaction notes

Loading…