Picilorex → HCID 86734443, compound

Reaction equation

[CH:1]1([CH:4]2[CH2:8][CH:7]([C:9]3[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=3)[CH:6]([CH3:16])[NH:5]2)[CH2:3][CH2:2]1.Br[CH:18]([OH:20])[CH3:19]>>[ClH:15].[OH:20][CH2:18][CH2:19][N:5]1[CH:6]([CH3:16])[CH:7]([C:9]2[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=2)[CH2:8][CH:4]1[CH:1]1[CH2:3][CH2:2]1

Participants

Reactant 2

HCID 191657Picilorex

HCID 14202443Ethanol, 1-bromo-

Product 1

HCID 86734443HCID 86734443, compoundYield 65.6%

Procedure

The procedure of Example XXXV using 15 g of 2-cyclopropyl-4-(p-chlorophenyl)-5-methyl-pyrrolidine and 8.8 g of bromoethanol gives 6.6 g of N-hydroxyethyl-2-cyclopropyl-4-(p-chlorophenyl)-5-methylpyrrolidine hydrochloride as white crystals after recrystallisation from ethyl acetate -- acetone (50:50). Melting point = 175°-180° C.

Sources & evidence

ORD record: ord-4a6cdb599e2d4d79abd55b4ff5fa8a6d
Source dataset: uspto-grants-1977_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04005103

Reaction notes

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