4-Methoxybenzaldehyde → HCID 45275023, compound

HRID 1622344Notes

Reaction equation

HRID 1622344 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].[CH3:21][O:22][C:23]1[CH:24]=[CH:25][C:26]([CH:29]=O)=[CH:27][CH:28]=1.C([BH3-])#N.[Na+]>CO>[Cl:19][C:18]1[CH:17]=[N:16][CH:15]=[C:14]([Cl:20])[C:13]=1[N:10]1[CH2:9][CH2:8][CH:7]([C:5]([NH:4][CH2:3][CH2:2][NH:1][CH2:29][C:26]2[CH:25]=[CH:24][C:23]([O:22][CH3:21])=[CH:28][CH:27]=2)=[O:6])[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 312444-MethoxybenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 45275021HCID 45275021, compound

Product 1

HCID 45275023HCID 45275023, compoundYield 19%

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 anisaldehyde (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 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 (13 mg, 19%), umax (CHCl3)/cm−1 3008, 2839, 1660, 1513, 1249, 1174, 1036; m/z (ESI) C21H27Cl2N4O2 requires 437.1506, found [M+H]+ 437.1508.

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-db0d5f9b229740e3a57a68ff96f332f6
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

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