Dimethylformamide → 4-[3-[4-[Bis(4-methoxyphenyl)methyl]-1-piperidinyl]propoxy]benzoic acid ethyl ester fumarate hydrate

HRID 1193682Notes

Reaction equation

HRID 1193682 reaction equation
CN(C)[CH:3]=[O:4].[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[CH:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[CH:10][CH:9]=1.[CH2:29]([O:31][C:32](=[O:44])[C:33]1[CH:38]=[CH:37][C:36]([O:39][CH2:40][CH2:41][CH2:42]Cl)=[CH:35][CH:34]=1)[CH3:30]>C(O)CCC>[OH2:4].[C:3]([OH:4])(=[O:7])/[CH:34]=[CH:33]/[C:32]([OH:44])=[O:31].[CH2:29]([O:31][C:32](=[O:44])[C:33]1[CH:38]=[CH:37][C:36]([O:39][CH2:40][CH2:41][CH2:42][N:18]2[CH2:19][CH2:20][CH:15]([CH:14]([C:21]3[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=3)[C:11]3[CH:10]=[CH:9][C:8]([O:7][CH3:6])=[CH:13][CH:12]=3)[CH2:16][CH2:17]2)=[CH:35][CH:34]=1)[CH3:30]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 144071674-[Bis(4-methoxyphenyl)methyl]piperidineHCID 18348522Ethyl 4-(3-chloropropoxy)benzoate

Product 1

HCID 703733334-[3-[4-[Bis(4-methoxyphenyl)methyl]-1-piperidinyl]propoxy]benzoic acid ethyl ester fumarate hydrate

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Following the procedure of Example 22, but substituting dimethylformamide at 73° C. for butanol, 4-[bis(4-methoxyphenyl)methyl]piperidine and 4-(3-chloropropoxy)benzoic acid ethyl ester were reacted to give the free base of the title compound which was reacted with fumaric acid, to give the white fumarate salt (recrystallizing from methanoldiethyl ether) in 27% yield, m.p. 147.5°-148.5° C.

Workup

  1. customat 73° C.
  2. customwere reacted

Sources & evidence

ORD record
ord-16a41b2c2b374449a63b131dcf11d5bb
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

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