Trifluoroacetic acid → 3-(4-(2-(Dimethylamino)ethyl)piperidine-4-carboxamido)phenyl dimethylcarbamate

HRID 216075Notes

Reaction equation

HRID 216075 reaction equation
[CH3:1][N:2]([CH3:33])[CH2:3][CH2:4][C:5]1([C:18](=[O:32])[NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][C:27](=[O:31])[N:28]([CH3:30])[CH3:29])[CH:21]=2)[CH2:10][CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7][CH2:6]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:30][N:28]([CH3:29])[C:27](=[O:31])[O:26][C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([NH:19][C:18]([C:5]2([CH2:4][CH2:3][N:2]([CH3:33])[CH3:1])[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)=[O:32])[CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67036855HCID 67036855, compound

Product 1

HCID 670372303-(4-(2-(Dimethylamino)ethyl)piperidine-4-carboxamido)phenyl dimethylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Crude tert-butyl 4-(2-(dimethylamino)ethyl)-4-(3-(dimethylcarbamoyloxy)phenylcarbamoyl)piperidine-1-carboxylate from step C was treated with 1:1 TFA:CH2Cl2 (1.5 mL) for 45 min. The reaction was concentrated under vacuum, and the residue was purified by prep HPLC (30×100 mm C18 column, 0-50% MeOH:H2O (0.1% TFA), 12 min., 45 mL/min.) and lyophized to give impure title compound (173 mg) as the TFA salt. MS (ES+) [M+H]+=363.

Workup

  1. concentrationThe reaction was concentrated under vacuum
  2. customthe residue was purified by prep HPLC (30×100 mm C18 column, 0-50% MeOH:H2O (0.1% TFA), 12 min., 45 mL/min.)

Sources & evidence

ORD record
ord-d2ceb76b33164d1bbbb64180afb66b1b
Source dataset
uspto-grants-2012_06
Patent number
US08193202B2

Reaction notes

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