Water → HCID 20453079, compound

HRID 1462388Notes

Reaction equation

HRID 1462388 reaction equation
Cl.[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][CH2:16][CH:15]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25]C)[CH:20]=3)[CH2:14]2)=[CH:3]1.O>ClCCl>[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][CH2:16][CH:15]([C:19]3[CH:20]=[C:21]([OH:25])[CH:22]=[CH:23][CH:24]=3)[CH2:14]2)=[CH:3]1

Participants

4

Reactant 2

HCID 962WaterHCID 20453058HCID 20453058, compound

Product 1

HCID 20453079HCID 20453079, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-[2-(1H-indol-3-yl)ethyl]-3-(3-methoxy phenyl) piperidine hydrochloride (1.4 g) in dichloromethane (500 ml) at -78° C. was treated dropwise with borontribromide (8 g) and the solution was allowed to warm up to room temperature over 2.5 hour. Water (5 ml) was added cautiously and the precipitate was filtered, washed with dichloromethane and water, dissolved in 10% sodium hydroxide solution (25 ml), acidified to pH 10 with 5N hydrochloric acid. The precipitate was collected, washed with water, to give 3-(1-[2-(1H-3-indolyl) ethyl]-3-piperidyl) phenol 1.2 g, m.p. 130°-135° C.

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed with dichloromethane and water
  3. dissolutiondissolved in 10% sodium hydroxide solution (25 ml)
  4. customThe precipitate was collected
  5. washwashed with water

Sources & evidence

ORD record
ord-9516ad8ff41e4c7d9ef3036570db9182
Source dataset
uspto-grants-1984_07
Patent number
US04460594

Reaction notes

Loading…