Hydrochloric Acid → HCID 67235730, compound

HRID 1039031Notes

Reaction equation

HRID 1039031 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[NH:15][C:16]3[C:21]([CH:22]=2)=[CH:20][C:19]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[CH:24]=2)=[CH:18][CH:17]=3)[CH2:10][CH2:9]1)=O)(C)(C)C.ClCCl.Cl>C(OCC)C>[CH3:32][O:31][C:25]1[CH:24]=[C:23]([C:19]2[CH:20]=[C:21]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14]([CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[CH:22]3)[CH:28]=[CH:27][C:26]=1[O:29][CH3:30]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 67236014HCID 67236014, compound

Product 1

HCID 67235730HCID 67235730, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 50 mL round bottom flask was charged with 4-[5-(3,4-dimethoxy-phenyl)-1H-indol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (500 mg, 1.15 mmol), dichloromethane (5.8 mL), and 1M hydrochloric acid in diethyl ether (5.8 mL) and the resulting mixture stirred for 2 h. The resulting mixture was then concentrated in vacuo, the residue triturated with diethyl ether, and then placed under high vacuum to yield 5-(3,4-dimethoxyphenyl)-2-(piperidin-4-yl)-1H-indole. 1H NMR (300 MHz, DMSO-d6) δ 7.69 (s, 1H), 7.29-7.37 (m, 2H), 7.09-7.22 (m, 2H), 6.99 (d, J=8.2 Hz, 1H), 6.22 (s, 1H), 3.84 (s, 3H), 3.78 (s, 3H), 3.67-3.74 (m, 1H), 3.02-3.15 (m, 4H), 2.50-2.61 (m, 2H), and 1.81-2.01 (m, 2H); MS (ES+) 337 (M+1).

Workup

  1. concentrationThe resulting mixture was then concentrated in vacuo
  2. customthe residue triturated with diethyl ether

Sources & evidence

ORD record
ord-72b300c86d964f95a2aebd359b2a8724
Source dataset
uspto-grants-2013_10
Patent number
US08552032B2

Reaction notes

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