Ethanol → 1,1-Dimethylethyl 4-[4-(cyclopropylmethyl)-1-piperazinyl]-1-piperidinecarboxylate

HRID 644324Notes

Reaction equation

HRID 644324 reaction equation
C([BH3-])#N.[Na+].Cl.Cl.[N:7]1([CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.[CH:26]1([CH:29]=O)[CH2:28][CH2:27]1.CCO>CO>[CH:26]1([CH2:29][N:10]2[CH2:9][CH2:8][N:7]([CH:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)[CH2:12][CH2:11]2)[CH2:28][CH2:27]1

Participants

6

Reactant 4

HCID 702EthanolHCID 123114CyclopropanecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 68579096686298-02-2

Product 1

HCID 685791711,1-Dimethylethyl 4-[4-(cyclopropylmethyl)-1-piperazinyl]-1-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.26 g (20.0 mmol) sodium cyanoborohydride was added batchwise at RT to a stirred mixture of 1.71 g (5.0 mmol) tert-butyl 4-piperazin-1-yl-piperidine-1-carboxylate dihydrochloride, 0.75 mL (10.0 mmol) cyclopropanecarbaldehyde, 30 mL EtOH and 20 mL MeOH and stirred overnight at RT. The reaction mixture was evaporated down under reduced pressure, the residue was taken up in saturated NaHCO3 solution and extracted erschöpfend with EtOAc. The combined organic phases were dried over Na2SO4, suction filtered, evaporated down under reduced pressure and purified by column chromatography over silica gel.

Workup

  1. customThe reaction mixture was evaporated down under reduced pressure
  2. extractionextracted erschöpfend with EtOAc
  3. dry with materialThe combined organic phases were dried over Na2SO4, suction
  4. filtrationfiltered
  5. customevaporated down under reduced pressure
  6. custompurified by column chromatography over silica gel

Sources & evidence

ORD record
ord-f579dbfad8154c16a7b450bf481f9d30
Source dataset
uspto-grants-2010_04
Patent number
US07700589B2

Reaction notes

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