Trifluoroacetic acid → HCID 89676828, compound

HRID 2278224Notes

Reaction equation

HRID 2278224 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[C:6]([CH2:8][N:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)[CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[C:6]([CH2:8][N:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]2)[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 896771271-Piperazinecarboxylic acid, 4-[[5-chloro-2-(4-morpholinyl)phenyl]methyl]-, 1,1-dimethylethyl ester

Product 1

HCID 89676828HCID 89676828, compoundYield 120.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A 100 mL round-bottom flask was charged with tert-butyl 4-[[5-chloro-2-(morpholin-4-yl)phenyl]methyl]piperazine-1-carboxylate (2.90 g, 7.32 mmol, 1.00 equiv), dichloromethane (35 mL). The mixture was cooled to 0° C. and trifluoroacetic acid (7 mL) was added dropwise. The resulting solution was stirred overnight at room temperature. The resulting solution was concentrated under reduced pressure to yield 2.60 g (crude) of 4-[4-chloro-2-(piperazin-1-ylmethyl)phenyl]morpholine as light yellow oil. LCMS (ESI, m/z): 296 [M+H]+.

Workup

  1. concentrationThe resulting solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3eb36aa30e5e40d1935f94d5ccc620a6
Source dataset
uspto-grants-2015_09
Patent number
US09133148B2

Reaction notes

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