Piperidine → HCID 86761960, compound

HRID 453901Notes

Reaction equation

HRID 453901 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH:15]=O)[CH:11]=2)[CH2:6]1)=[O:4].[NH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.ClCCl.C(=O)([O-])O.[Na+]>[F:1][C:2]([F:18])([F:17])[C:3]([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH2:15][N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:11]=2)[CH2:6]1)=[O:4]

Participants

7

Reactant 3

HCID 8082PiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 75176179HCID 75176179, compound

Product 1

HCID 86761960HCID 86761960, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

2-(2,2,2-Trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline-6-carbaldehyde (2 g, 7.78 mmol) and piperidine (660 mg, 7.78 mmol) were dissolved in 1,2-dichloroethane (24 ml), and sodium triacetoxyborohydride (2.29 g, 10.89 mmol) was added. The reaction mixture was stirred for 15 h, then diluted with dichloromethane, and sat. sodium hydrogen carbonate solution (100 ml) was added. After phase separation, the aqueous phase was extracted with dichloromethane (3×100 ml). The combined organic phases were washed with sat. sodium chloride solution (50 ml), dried over magnesium sulfate and concentrated under vacuum. The crude product was purified by column chromatography (silica gel, ethyl acetate/dichloromethane/methanol 10:1:1+ammonia solution (25% aq.)). Yield: 1.88 g (74%)

Workup

  1. additionwas added
  2. customAfter phase separation
  3. extractionthe aqueous phase was extracted with dichloromethane (3×100 ml)
  4. washThe combined organic phases were washed with sat. sodium chloride solution (50 ml)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe crude product was purified by column chromatography (silica gel, ethyl acetate/dichloromethane/methanol 10:1:1+ammonia solution (25% aq.))

Sources & evidence

ORD record
ord-45ab9fd4b11942d0909b92d09cea6f09
Source dataset
uspto-grants-2013_07
Patent number
US08492559B2

Reaction notes

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