Water → HCID 13180291, compound

HRID 867015Notes

Reaction equation

HRID 867015 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:5]=1[C:6]([CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7].C(N(CC)CC)C.Br[CH2:28][CH2:29][C:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[NH:32][CH:31]=1.O>CN(C)C=O>[CH3:2][O:3][C:4]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:5]=1[C:6]([CH:8]1[CH2:9][CH2:10][N:11]([CH2:28][CH2:29][C:30]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[NH:32][CH:31]=2)[CH2:12][CH2:13]1)=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 769243-(2-Bromoethyl)indoleHCID 20311698HCID 20311698, compound

Product 1

HCID 13180291HCID 13180291, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirring solution of 8.0 g of 4-(2,4-dimethoxybenzoyl)piperidine hydrochloride and 6 ml of triethylamine in 250 ml of dimethylformamide is added a solution of 6.4 g of 3-(2-bromoethyl)indole in 50 ml of dimethylformamide. The reaction mixture is permitted to stir at ambient temperature for 72 hours and then 500 ml of water is added dropwise and extracted with chloroform. The combined extracts are dried and most of the chloroform removed leaving a dark oil. The oil is subjected to column chromotography on a silica gel column and eluting with a 3% methanol in chloroform solution to give 3-{2-[4-(2,4-dimethoxybenzoyl)piperidyl]ethyl}indole. The indole is recrystallized thrice from an ethanol-water mixture to give the pure indole, mp 110°-112° C.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe combined extracts are dried and most of the chloroform
  3. customremoved
  4. customleaving a dark oil
  5. washeluting with a 3% methanol in chloroform solution

Sources & evidence

ORD record
ord-14c47ee9dd60458eabd0b2e9c15e9380
Source dataset
uspto-grants-1978_07
Patent number
US04101663

Reaction notes

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