Methanesulfonate → 1'-[4-(2-chloro-5-trifluoromethylbenzoyl)-1-butyl]-spiro[isobenzofuran-1(3H),4'-piperidine]

HRID 378549Notes

Reaction equation

HRID 378549 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:3]=1[C:4]([CH2:6][CH2:7][CH2:8][CH2:9]O)=[O:5].CS([O-])(=O)=O.[NH:24]1[CH2:29][CH2:28][C:27]2([C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:31][O:30]2)[CH2:26][CH2:25]1>>[Cl:1][C:2]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:3]=1[C:4]([CH2:6][CH2:7][CH2:8][CH2:9][N:24]1[CH2:29][CH2:28][C:27]2([C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:31][O:30]2)[CH2:26][CH2:25]1)=[O:5]

Participants

4

Reactant 3

HCID 85257MethanesulfonateHCID 104424983H-spiro[2-benzofuran-1,4'-piperidine]HCID 220121644-(2-Chloro-5-trifluoromethylbenzoyl)-1-butanol

Product 1

HCID 220122171'-[4-(2-chloro-5-trifluoromethylbenzoyl)-1-butyl]-spiro[isobenzofuran-1(3H),4'-piperidine]

Procedure

4-(2-Chloro-5-trifluoromethylbenzoyl)-1-butanol, prepared as described in EXAMPLE 17, was converted to the corresponding methanesulfonate by the method described in EXAMPLE 2. Treatment with spiro[isobenzofuran-1(3H),4'-piperidine] according to the method described in EXAMPLE 2 gave 1'-[4-(2-chloro-5-trifluoromethylbenzoyl)-1-butyl]-spiro[isobenzofuran-1(3H),4'-piperidine]. Conversion to the corresponding hydrazone and ring closure according to the method described in EXAMPLE 17 gave the title compound, 18, mp: 146-47° C.

Sources & evidence

ORD record
ord-5464a6d395c04792828a26c8b6dfa6e8
Source dataset
uspto-grants-2000_02
Patent number
US06031099

Reaction notes

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