3-(4-Chlorophenoxy)pyrrolidine → N-{2-[(3-[3-[(4-Chlorophenyl)oxy]-1-pyrrolidinyl}-2-hydroxy-1-methylpropyl)oxy]phenyl}acetamide Hydrochloride

HRID 584643Notes

Reaction equation

HRID 584643 reaction equation
[O:1]1[CH2:3][CH:2]1[CH:4]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14](=[O:16])[CH3:15])[CH3:5].[Cl:17][C:18]1[CH:29]=[CH:28][C:21]([O:22][CH:23]2[CH2:27][CH2:26][NH:25][CH2:24]2)=[CH:20][CH:19]=1>>[ClH:17].[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([O:22][CH:23]2[CH2:27][CH2:26][N:25]([CH2:3][CH:2]([OH:1])[CH:4]([O:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[NH:13][C:14](=[O:16])[CH3:15])[CH3:5])[CH2:24]2)=[CH:28][CH:29]=1

Participants

3

Reactant 2

HCID 129995703-(4-Chlorophenoxy)pyrrolidineHCID 22313695N-[2-(1-oxiranylethoxy)phenyl]acetamide

Product 1

HCID 22313656N-{2-[(3-[3-[(4-Chlorophenyl)oxy]-1-pyrrolidinyl}-2-hydroxy-1-methylpropyl)oxy]phenyl}acetamide HydrochlorideYield 100%

Procedure

The title compound (230 mg, 100%) was prepared from N-[2-(1-oxiranylethoxy)phenyl]acetamide diasteromer 2 (123 mg, 0.557 mmol) and 3-(4-chlorophenoxy)pyrrolidine (100 mg, 0.506 mmol) analogously to that described in Example 1 (iii).

Sources & evidence

ORD record
ord-6a33480cbff64924bf4d899f4c97ab19
Source dataset
uspto-grants-2005_08
Patent number
US06927222B2

Reaction notes

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