Trifluoroacetic acid → (4-Amino-phenyl)-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]oct-6-yl)-methanone

HRID 643254Notes

Reaction equation

HRID 643254 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([N:16]2[CH2:22][C:21]3([CH3:24])[CH2:23][CH:17]2[CH2:18][C:19]([CH3:26])([CH3:25])[CH2:20]3)=[O:15])=[CH:10][CH:9]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]([N:16]2[CH2:22][C:21]3([CH3:24])[CH2:23][CH:17]2[CH2:18][C:19]([CH3:26])([CH3:25])[CH2:20]3)=[O:15])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 9907515[4-(1,3,3-Trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-phenyl]carbamic acid tert-butyl ester

Product 1

HCID 577868(4-Amino-phenyl)-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]oct-6-yl)-methanoneYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [4-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-phenyl]carbamic acid tert-butyl ester (11.78 g, 31.61 mmol) in DCM (150 ml) was added TFA (50 ml). The resulting mixture was stirred for 48 hrs. at room temperature and evaporated in vacuo. To the residue was added water (150 ml) and diethyl ether (50 ml) and the pH was adjusted to 8 by addition of 32% aq. sodium hydroxide. The mixture was stirred for 15 min., the precipitate filtered off, washed with water and dried in vacuo at 50° C. for 18 hrs. affording 8.4 g (98%) of the title compound as a solid.

Workup

  1. customat room temperature and evaporated in vacuo
  2. additionTo the residue was added water (150 ml) and diethyl ether (50 ml)
  3. additionthe pH was adjusted to 8 by addition of 32% aq. sodium hydroxide
  4. stirringThe mixture was stirred for 15 min.
  5. filtrationthe precipitate filtered off
  6. washwashed with water
  7. customdried in vacuo at 50° C. for 18 hrs

Sources & evidence

ORD record
ord-fae82ed0ba2c4b8e816ac8266ecebaa3
Source dataset
uspto-grants-2010_04
Patent number
US07700583B2

Reaction notes

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