tert-Butyl 4-formylpiperidine-1-carboxylate → HCID 18328903, compound

HRID 1249720Notes

Reaction equation

HRID 1249720 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.Cl.[CH3:18][C:19]1[N:24]=[C:23]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:22]=[CH:21][N:20]=1.C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:28]2[CH2:29][CH2:30][N:25]([C:23]3[CH:22]=[CH:21][N:20]=[C:19]([CH3:18])[N:24]=3)[CH2:26][CH2:27]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 5003444Sodium cyanoborohydrideHCID 18328942Pyrimidine, 2-methyl-4-(1-piperazinyl)-, hydrochloride (1:2)

Product 1

HCID 18328903HCID 18328903, compoundYield 24.1%

Reagents, catalysts & solvents 1

HCID 10129899Acetic acid methanolSolvent

Procedure

To a solution of 1-(tert-butoxycarbonyl)-4-(formyl)piperidine (7.14 g) and 1-(2-methylpyrimidin-4-yl)piperazine dihydrochloride (8.38 g) in methanol/acetic acid (99:1) (150 ml) was added sodium cyanoborohydride (6.32 g) portionwise over 30 minutes and the resultant suspension stirred at arnbient temperature for 3 hours. The suspension was quenched by addition of saturated aqueous sodium bicarbonate solution and the resulting mixture extracted with ethyl acetate. The organic phase was dried (Na2SO4) and evaporated. The residue was purified by chromatography eluting with 5% methanol in dichloromethane to give 1-tert-butoxycarbonyl-4-[1-(2-methylpyrimidin-4-yl)piperazin-4-ylmethyl]piperidine (3.02 g) as a foam.

Workup

  1. customThe suspension was quenched by addition of saturated aqueous sodium bicarbonate solution
  2. extractionthe resulting mixture extracted with ethyl acetate
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customevaporated
  5. customThe residue was purified by chromatography
  6. washeluting with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-0ab5f0d385e94395a29e5583357d3447
Source dataset
uspto-grants-2002_01
Patent number
US06335341B1

Reaction notes

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