Acetic Acid → 4-(N-(2-methyl-3-phenyl-2-(E)-propenyl)aminomethyl)-1-(1-naphthylsulfonyl)piperidine

HRID 2110834Notes

Reaction equation

HRID 2110834 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([S:9]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH2:5][CH2:4]1.[CH3:22]/[C:23](=[CH:26]\[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)/[CH:24]=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>CCCCCC.C(OCC)(=O)C.ClCCCl>[CH3:22]/[C:23](=[CH:26]\[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)/[CH2:24][NH:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([S:9]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH2:5][CH2:4]1

Participants

9

Reactant 5

HCID 176Acetic Acid2×HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 5372813alpha-METHYLCINNAMALDEHYDEHCID 688620304-Aminomethyl-1-(1-naphthylsulfonyl)piperidine

Product 1

HCID 688606314-(N-(2-methyl-3-phenyl-2-(E)-propenyl)aminomethyl)-1-(1-naphthylsulfonyl)piperidineYield 86%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of 4-aminomethyl-1-(1-naphthylsulfonyl)piperidine (intermediate in the preparation of the compound of Example 34, 450 mg, 1.5 mmol), (E)-2-methyl-3-phenylpropenal (438 mg, 3.0 mmol), acetic acid (240 mg, 4.0 mmol), and 1,2-dichloroethane (50 mL) was stirred under argon at room temperature for 3 h before sodium triacetoxyborohydride (1.27 g, 6.0 mmol) and more acetic acid (360 mg, 6.0 mmol) were added. After 16 h saturated aqueous sodium bicarbonate (50 mL) was added, and the aqueous and organic phases were separated. The aqueous phase was extracted with dichloromethane (50 mL twice), and the combined organic phases were dried (anhydrous sodium sulfate) and evaporated under vacuum. Column chromatography (silica gel, gradient of ethyl acetate in hexane rising to 100% ethyl acetate) provided 4-(N-(2-methyl-3-phenyl-2-(E)-propenyl)aminomethyl)-1-(1-naphthylsulfonyl)piperidine (561 mg, 86% yield) as an oil. TLC Rf=0.18, 100% ethyl acetate.

Workup

  1. additionwere added
  2. customthe aqueous and organic phases were separated
  3. extractionThe aqueous phase was extracted with dichloromethane (50 mL twice), and the combined organic phases
  4. dry with materialwere dried (anhydrous sodium sulfate)
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-6996b9f5ac424b85ae41fb171e202bc7
Source dataset
uspto-grants-2009_04
Patent number
US07517991B2

Reaction notes

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