Cyclohexanecarboxaldehyde → HCID 67339402, compound

HRID 1622345Notes

Reaction equation

HRID 1622345 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]1([CH:27]=O)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.C([BH3-])#N.[Na+]>CO>[CH:21]1([CH2:27][NH:1][CH2:2][CH2:3][NH:4][C:5]([CH:7]2[CH2:8][CH2:9][N:10]([C:13]3[C:14]([Cl:20])=[CH:15][N:16]=[CH:17][C:18]=3[Cl:19])[CH2:11][CH2:12]2)=[O:6])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 16275CyclohexanecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 45275021HCID 45275021, compound

Product 1

HCID 67339402HCID 67339402, compoundYield 23%

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 cyclohexanecarbaldehyde (19 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 16 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 white solid (15 mg, 23%), m.p. 174-177° C.; umax (CHCl3)/cm−1 2932, 2856, 1665, 1558, 1457, 1236, 1146, 1037; m/z (ESI) C20H31Cl22N4O requires 413.1869, found [M+H]+ 413.1875.

Workup

  1. stirringthe mixture was stirred for a further 16 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-6e1475ba4fdc4272a5d6e307bf298d06
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

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