Hydrochloric Acid → (S)-1-{4-[Bis-(4-fluoro-phenyl)-methyl]-piperazin-1-ylmethyl}-3-methyl-butylamine monohydrochloride

HRID 990364Notes

Reaction equation

HRID 990364 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH2:13][N:14]1[CH2:19][CH2:18][N:17]([CH:20]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[CH2:16][CH2:15]1)[CH2:9][CH:10]([CH3:12])[CH3:11])(C)(C)C.FC(F)(F)C(O)=O.[ClH:43]>C(Cl)Cl.CCOCC>[ClH:43].[F:27][C:24]1[CH:25]=[CH:26][C:21]([CH:20]([C:28]2[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=2)[N:17]2[CH2:16][CH2:15][N:14]([CH2:13][C@@H:8]([NH2:7])[CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:19][CH2:18]2)=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 53854298(S)-(1-{4-[Bis-(4-fluoro-phenyl)-methyl]-piperazin-1-ylmethyl}-3-methyl-butyl)-carbamic acid tert-butyl ester

Product 1

HCID 70157127(S)-1-{4-[Bis-(4-fluoro-phenyl)-methyl]-piperazin-1-ylmethyl}-3-methyl-butylamine monohydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

(S)-(1-{4-[Bis-(4-fluoro-phenyl)-methyl]-piperazin-1-ylmethyl}-3-methyl-butyl)carbamic acid tert-butyl ester (0.225 g, 0.461 mmol, Example 35) was dissolved in CH2Cl2 (4 mL) under nitrogen at ambient temperature. To this solution was added trifluoroacetic acid (0.5 mL). The resulting reaction mixture was stirred for 3 hours, then concentrated in vacuo. The viscous pale-amber oil obtained was dissolved in 5 mL of ether and treated with 3.3 mL of saturated ethereal HCl. The resulting white precipitate was triturated with 3:1 EtOAc/2,2,4-trimethylpentane, and collected via filtration. The filtrate was concentrated in vacuo affording a viscous amber oil (189 mg) which was used in the subsequent reaction without further purification.

Workup

  1. customThe resulting reaction mixture
  2. concentrationconcentrated in vacuo
  3. customThe viscous pale-amber oil obtained
  4. customThe resulting white precipitate was triturated with 3:1 EtOAc/2,2,4-trimethylpentane
  5. filtrationcollected via filtration
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-2a087228736c4bfea96333c63a01c1be
Source dataset
uspto-grants-2002_10
Patent number
US06458781B1

Reaction notes

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