Ammonium formate → HCID 58860694, compound

HRID 1350405Notes

Reaction equation

HRID 1350405 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11](CC2C=CC=CC=2)[CH2:10][C@@H:9]1[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]([F:32])([F:31])[F:30])C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].C(O)C>[F:32][C:29]([F:30])([F:31])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[CH2:22][CH2:21][C@H:9]1[CH2:10][NH:11][CH2:12][CH2:13][NH:8]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 58860682HCID 58860682, compound

Product 1

HCID 58860694HCID 58860694, compoundYield 93.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Combine (S)-1,4-dibenzyl-2-[2-(2-trifluoromethyl-phenyl)-ethyl]-piperazine (2.66 g, 6.06 mmol), ammonium formate (1.91 g, 30.31 mmol), 5% Pd/C (293.3 mg), and ethanol (100 ml). Stir and heat the mixture at reflux. After 3 hrs, cool to ambient temperature and remove the catalyst by vacuum filtration through celite. Reduce the filtrate to residue. Purify the residue on silica gel using dichloromethane/2N ammonia in methanol (90:10) to give 1.46 g (93%) of the title compound as a white solid: mp 43°–47°; mass spectrum (ion spray): m/z=259.2 (M+1).

Workup

  1. temperatureheat the mixture
  2. temperatureat reflux
  3. customremove the catalyst
  4. filtrationby vacuum filtration through celite
  5. customPurify the residue on silica gel

Sources & evidence

ORD record
ord-b27b219cb6f941e2b23a3bca608d48a8
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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