Chlorobenzene → HCID 69330605, compound

HRID 2299698Notes

Reaction equation

HRID 2299698 reaction equation
Cl.C([N:9]([CH2:23][C@@H:24]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=1)[OH:25])[CH:10]1[CH2:16][CH2:15][CH2:14][C:13]2[CH:17]=[CH:18][C:19]([O:21][CH3:22])=[CH:20][C:12]=2[CH2:11]1)C1C=CC=CC=1.ClC1C=CC=CC=1>[Pd].CO>[ClH:32].[CH3:22][O:21][C:19]1[CH:18]=[CH:17][C:13]2[CH2:14][CH2:15][CH2:16][CH:10]([NH:9][CH2:23][C@@H:24]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=3)[OH:25])[CH2:11][C:12]=2[CH:20]=1

Participants

5

Reactant 2

HCID 7964ChlorobenzeneHCID 69330025HCID 69330025, compound

Product 1

HCID 69330605HCID 69330605, compoundYield 173%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (1R)-2-[N-benzyl-N-(3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino]-1-(3-chlorophenyl)ethanol hydrochloride (0.20 g), chlorobenzene (0.86 ml) and 10% palladium on carbon (0.01 g) in methanol (4 ml) was stirred at room temperature under hydrogen atmosphere for 1.5 hours. The catalyst was filtered off and washed with methanol. The filtrate was evaporated in vacuo, and the residue was powdered from diisopropyl ether to afford (1R)-2-[(3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino]-1-(3-chlorophenyl)ethanol hydrochloride (0.14 g)

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with methanol
  3. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-c9444059366e42ff97df5e3bc7c02dc6
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

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