3-(Trifluoromethyl)phenyl chloroformate → 3-(Trifluoromethyl)phenyl 4-(prop-2-ynyl)piperidine-1-carboxylate

HRID 1514045Notes

Reaction equation

HRID 1514045 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:6]=1)=[O:3].[CH2:15]([CH:18]1[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]1)[C:16]#[CH:17]>>[CH2:15]([CH:18]1[CH2:23][CH2:22][N:21]([C:2]([O:4][C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:6]=2)=[O:3])[CH2:20][CH2:19]1)[C:16]#[CH:17]

Participants

3

Reactant 2

HCID 50574253-(Trifluoromethyl)phenyl chloroformateHCID 18187546Tert-butyl 4-(prop-2-yn-1-yl)piperidine-1-carboxylate

Product 1

HCID 578389003-(Trifluoromethyl)phenyl 4-(prop-2-ynyl)piperidine-1-carboxylate

Procedure

3-(trifluoromethyl)phenyl chloroformate (5.0 g, 29.3 mmol) was added to a solution of tert-butyl 4-(prop-2-ynyl)piperidine-1-carboxylate (1.50 g, 6.72 mmol) according to general procedure 1. Yield=1.1031 g, 64%. m/z MH+=302.02. HPLC rt=10.8 min.

Workup

  1. customHPLC rt=10.8 min.

Sources & evidence

ORD record
ord-3af6dea1e8294ec0af833a80aab5b541
Source dataset
uspto-grants-2012_07
Patent number
US08222228B2

Reaction notes

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