Trifluoroacetic acid → Ammonia

HRID 2178891Notes

Reaction equation

HRID 2178891 reaction equation
[CH3:1][N:2]([CH3:17])[C@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9]C(=O)OC(C)(C)C)[CH2:5][CH2:4]1.C(O)(C(F)(F)F)=O>>[NH3:2].[CH3:1][N:2]([CH3:17])[C@H:3]1[CH2:8][CH2:7][C@H:6]([NH2:9])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178484112HCID 178484112, compound

Product 2

HCID 222AmmoniaHCID 178484105HCID 178484105, compound

Conditions

Temperature
75 °C

Procedure

To a solution of tert-butyl trans-4-(dimethylamino)cyclohexylcarbamate (800 mg, 3.3 mmol) was added TFA (5 mL) and the reaction mixture was stirred with heat at 75° C. for 18 h. The reaction mixture was concentrated, the residue was loaded onto an SCX® ion-exchange column, flushed with methanol and then 7 N ammonia in methanol to obtain the desired product. The fractions containing the product were concentrated to dryness to obtain the desired product as the free base (400 mg, 85%) as an orange oil: ESI MS m/z 143 [C8H18N2+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customflushed with methanol

Sources & evidence

ORD record
ord-35a57eb9759248ef8db0284262f9c51d
Source dataset
uspto-grants-2015_06
Patent number
US09067937B2

Reaction notes

Loading…