Sodium Bicarbonate → HCID 15480994, compound

HRID 1634320Notes

Reaction equation

HRID 1634320 reaction equation
Cl.Cl.[C:3]1([C@H:9]2[C@@H:14]([NH2:15])[CH2:13][CH2:12][CH2:11][NH:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:16][C:17]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][C:18]=1[CH:19]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:16][C:17]1[CH:24]=[CH:23][C:22]([C:25]([F:26])([F:27])[F:28])=[CH:21][C:18]=1[CH2:19][NH:15][C@H:14]1[CH2:13][CH2:12][CH2:11][NH:10][C@H:9]1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 6881812-Chloro-5-(trifluoromethyl)benzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 69654807(2S,3S)-2-Phenylpiperidin-3-amine dihydrochloride

Product 1

HCID 15480994HCID 15480994, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of Compound 1 (150 mg, 0.60 mmol) and 2-chloro-5-(trifluoromethyl)benzaldehyde (126 mg, 0.60 mmol) in dry CH2Cl2 (6 ml) was added NaBH(OAc)3 (179 mg, 0.84 mmol) portionwise under nitrogen at room temperature. The reaction mixture was stirred at room temperature for 17 hr. This was basified with sat. NaHCO3 aq., extracted with CH2Cl2, dried with MgSO4, and concentrated to give crude (2S,3S)-3-(2-chloro-5-(trifluoromethyl)benzyl)amino-2-phenylpiperidine as a colorless oil. This was purified with chromatography to give pure (2S,3S)-3-(2-chloro-5-(trifluoromethyl)benzyl)amino-2-phenylpiperidine as a colorless oil (135 mg). This was diluted with ethyl acetate, added HCl-MeOH, and concentrated. The white solid was recrystallized from MeOH to give Compound 3 as a white crystalline (64 mg, 24.1%).

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialdried with MgSO4
  3. concentrationconcentrated
  4. customto give crude (2S,3S)-3-(2-chloro-5-(trifluoromethyl)benzyl)amino-2-phenylpiperidine as a colorless oil
  5. customThis was purified with chromatography

Sources & evidence

ORD record
ord-7638c9aa4256422fb481b2a2b05e55a0
Source dataset
uspto-grants-2003_01
Patent number
US06506775B1

Reaction notes

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