Trifluoroacetic anhydride → HCID 22851568, compound

HRID 1736962Notes

Reaction equation

HRID 1736962 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]([O:5][C:6](=[O:11])[C:7]([F:10])([F:9])[F:8])=[O:4].[CH2:14]([N:21]1[CH2:26][CH2:25][CH:24]([NH2:27])[CH2:23][C@H:22]1[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(Cl)Cl>[F:1][C:2]([F:13])([F:12])[C:3]([OH:5])=[O:4].[CH2:14]([N:21]1[CH2:26][CH2:25][CH:24]([NH:27][C:6](=[O:11])[C:7]([F:8])([F:9])[F:10])[CH2:23][C@H:22]1[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 54441498HCID 54441498, compound

Product 1

HCID 22851568HCID 22851568, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.1 ml (36.8 mmol) of trifluoroacetic anhydride are added to a solution of 6.88 g (24.5 mmol) of (2R,4RS)-1,2-dibenzyl-4-piperidinamine in 20 ml of methylene chloride in an ice-water bath, and stirring is then completed at room temperature for 1 hour. The reaction mixture is evaporated to dryness, resulting in the title compound as pale yellow foam; TLC: methylene chloride/methanol/conc. ammonia (190:9:1), Rf =0.41 (cis) and 0.57 (trans) diastereomer; MS: M+ -91 (benzyl)=285 (14%).

Workup

  1. customThe reaction mixture is evaporated to dryness

Sources & evidence

ORD record
ord-d86f7dcb304c4b6b853b3cffd1d3824c
Source dataset
uspto-grants-1996_07
Patent number
US05541195

Reaction notes

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