Chlorobenzene → HCID 86628566, compound

HRID 732724Notes

Reaction equation

HRID 732724 reaction equation
[C:1]1([C@H:11]([N:13]([CH2:21][CH:22]2[CH:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:25][NH:24][CH2:23]2)[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.CC(C)([O-])C.[K+]>C1(C)C=CC=CC=1>[C:34]1([N:24]2[CH2:25][CH:26]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:22]([CH2:21][N:13]([C@@H:11]([C:1]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]=[CH:3][CH:2]=3)[CH3:12])[C:14](=[O:20])[O:15][C:16]([CH3:18])([CH3:19])[CH3:17])[CH2:23]2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 7964ChlorobenzeneHCID 23665647Potassium tert-butoxideHCID 86628564HCID 86628564, compound

Product 1

HCID 86628566HCID 86628566, compoundYield 33.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
135 °C

Procedure

In accordance with the techniques of “Journal of Organic Chemistry”, 2001, vol. 66, p. 1403-1412, a mixture of 215 mg of tert-butyl [(1R)-1-(1-naphthyl)ethyl][(4-phenylpyrrolidin-3-yl)methyl]carbamate, 113 mg of chlorobenzene and 3 ml of toluene was mixed with 231 mg of potassium tert-butoxide and heated at 135° C. for 36 hours in a sealed tube. The organic layer was washed with 1 M hydrochloric acid, and the organic layer was dried with anhydrous sodium sulfate and concentrated under a reduced pressure. The thus obtained residue was purified by a silica gel column chromatography (chloroform-methanol) to obtain 85 mg of tert-butyl [(1,4-diphenylpyrrolidin-3-yl)methyl][(1R)-1-(1-naphthyl)ethyl]carbamate as a colorless oily substance. The thus obtained compound was dissolved in 2 ml of ethyl acetate, mixed with 1 ml of 4 M hydrogen chloride/ethyl acetate and stirred at room temperature for 6 hours. The reaction solution was concentrated under a reduced pressure, and the thus precipitated solid was collected by filtration to obtain 30 mg of (1R)—N-[(1,4-diphenylpyrrolidin-3-yl)methyl]-1-(1-naphthyl)ethanamine dichloride as a purple solid.

Workup

  1. washThe organic layer was washed with 1 M hydrochloric acid
  2. dry with materialthe organic layer was dried with anhydrous sodium sulfate
  3. concentrationconcentrated under a reduced pressure
  4. customThe thus obtained residue was purified by a silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-45d948351e7a45d6908f75bc8aa16086
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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