Trifluoroacetic acid → HCID 89677377, compound

HRID 2278212Notes

Reaction equation

HRID 2278212 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:5]=[CH:4][C:3]=1[CH2:13][N:14]1[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:5]=[CH:4][C:3]=1[CH2:13][N:14]1[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89677045HCID 89677045, compound

Product 1

HCID 89677377HCID 89677377, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 50 mL round-bottom flask was charged with tert-butyl 4-[[2-chloro-4-(pyrrolidin-1-yl)phenyl]methyl]piperazine-1-carboxylate (0.270 g, 0.710 mmol, 1.00 equiv), dichloromethane (10 mL). Trifluoroacetic acid (3.00 g, 26.3 mmol, 37.00 equiv) was added at 0° C. The resulting solution was stirred overnight at room temperature and concentrated under reduced pressure to yield 0.160 g (crude) of 1-[[2-chloro-4-(pyrrolidin-1-yl)phenyl]methyl]piperazine as yellow oil. LCMS (ESI, m/z): 280 [M+H]+.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7eefa287f7e04caf8521d86da8314804
Source dataset
uspto-grants-2015_09
Patent number
US09133148B2

Reaction notes

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