Benzaldehyde → HCID 45275022, compound

HRID 1622343Notes

Reaction equation

HRID 1622343 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]([CH:7]1[CH2:12][CH2:11][N:10]([C:13]2[C:18]([Cl:19])=[CH:17][N:16]=[CH:15][C:14]=2[Cl:20])[CH2:9][CH2:8]1)=[O:6].[CH:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([BH3-])#N.[Na+]>CO>[CH2:21]([NH:1][CH2:2][CH2:3][NH:4][C:5]([CH:7]1[CH2:8][CH2:9][N:10]([C:13]2[C:14]([Cl:20])=[CH:15][N:16]=[CH:17][C:18]=2[Cl:19])[CH2:11][CH2:12]1)=[O:6])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 45275021HCID 45275021, compound

Product 1

HCID 45275022HCID 45275022, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(2-aminoethyl)-1-(3,5-dichloropyridin-4-yl)piperidine-4-carboxamide E13 (50 mg, 0.16 mmol) in MeOH (5 mL) was added benzaldehyde (16 μL, 0.16 mmol). After stirring for 2 h, sodium cyanoborohydride (20 mg, 0.32 mmol) was added and the mixture was stirred for a further 20 h. The solvent was removed under reduced pressure, the residue was dissolved in EtOAc (20 mL), washed with a saturated solution of sodium hydrogencarbonate (25 mL), brine (25 mL), dried (MgSO4) and the solvent was removed under reduced pressure. The crude product was purified by preparative tlc on silica gel (CH2Cl2, MeOH, 9:1) to furnish the title compound as a colourless oil (19 mg, 30%), umax (CHCl3)/cm−1 3015, 2850, 1659, 1558, 1512, 1236, 1146, 1036, 934; m/z (ESI) C20H25Cl2N4O requires 407.1400, found [M+H]+ 407.1401.

Workup

  1. stirringthe mixture was stirred for a further 20 h
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in EtOAc (20 mL)
  4. washwashed with a saturated solution of sodium hydrogencarbonate (25 mL), brine (25 mL)
  5. dry with materialdried (MgSO4)
  6. customthe solvent was removed under reduced pressure
  7. customThe crude product was purified by preparative tlc on silica gel (CH2Cl2, MeOH, 9:1)

Sources & evidence

ORD record
ord-fe4d193818824c1baa0b390dedd4744e
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

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