Maleic Acid → cis-4-amino-5-chloro-N-[1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl]-2-methoxybenzamide (Z)-2-butenedioate

HRID 1088409Notes

Reaction equation

HRID 1088409 reaction equation
[NH2:1][C:2]1[C:29]([Cl:30])=[CH:28][C:5]([C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[CH2:11][C@H:10]2[O:26][CH3:27])=[O:7])=[C:4]([O:31][CH3:32])[CH:3]=1.[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]\[C:36]([OH:38])=[O:37]>C(O)C>[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]\[C:36]([OH:38])=[O:37].[NH2:1][C:2]1[C:29]([Cl:30])=[CH:28][C:5]([C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][O:18][C:19]3[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=3)[CH2:11][C@H:10]2[O:26][CH3:27])=[O:7])=[C:4]([O:31][CH3:32])[CH:3]=1

Participants

4

Reactant 2

HCID 444266Maleic AcidHCID 53110474-amino-5-chloro-N-[(3R,4S)-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-yl]-2-methoxybenzamide

Product 1

HCID 86744272cis-4-amino-5-chloro-N-[1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl]-2-methoxybenzamide (Z)-2-butenedioateYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred solution of 4 parts of cis-4-amino-5-chloro-N-[1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl]-2-methoxybenzamide in 64 parts of ethanol was added a solution of 1 part of (Z)-2-butenedioic acid in 16 parts of ethanol and the product was allowed to crystallize. It is filtered off and dried, yielding 4.8 parts (92%) of cis-4-amino-5-chloro-N-[1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl]-2-methoxybenzamide (Z)-2-butenedioate (1:1); mp. 200.3° C. (compound 240).

Workup

  1. customto crystallize
  2. filtrationIt is filtered off
  3. customdried

Sources & evidence

ORD record
ord-5d74aaf4c35c48098938fe6133b6778b
Source dataset
uspto-grants-1990_10
Patent number
US04962115

Reaction notes

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