tert-Butyl piperazine-1-carboxylate → HCID 70153567, compound

HRID 1249726Notes

Reaction equation

HRID 1249726 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([CH:14]=O)[CH2:10][CH2:9]2)[CH:5]=[CH:4][N:3]=1.[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17].C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][N:26]([CH2:14][CH:11]2[CH2:10][CH2:9][N:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[N:7]=3)[CH2:13][CH2:12]2)[CH2:25][CH2:24]1)=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 5003444Sodium cyanoborohydrideHCID 18328946HCID 18328946, compound

Product 1

HCID 70153567HCID 70153567, compoundYield 36.7%

Reagents, catalysts & solvents 1

HCID 10129899Acetic acid methanolSolvent

Procedure

To a solution of 1-(2-methylpyrimidin-4-yl)-4-(formyl)piperidine (4.25 g) and N-t-butoxycarbonyl piperazine (5.34 g) in methanol/acetic acid (99:1) (100 ml) was added sodium cyanoborohydride (5.41 g) portionwise over 30 minutes and the resultant suspension stirred at ambient 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 10% methanol in ethylacetate to give 1-(tert-butoxycarbonyl)-4-[1-(2-methylpyrimidin-4-yl)-4-piperidylmethyl]piperazine (2.85 g) as a solid.

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 10% methanol in ethylacetate

Sources & evidence

ORD record
ord-d96dc4c2d5e947dab386c27b18ade346
Source dataset
uspto-grants-2002_01
Patent number
US06335341B1

Reaction notes

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