p-Toluidine → para-methyl 4-Anilino-1-Boc-piperidine

HRID 2223876Notes

Reaction equation

HRID 2223876 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1.C(O)(=O)C>[C:19]1([CH3:22])[CH:20]=[CH:21][C:16]([NH:15][CH:2]2[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]2)=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 7813p-ToluidineHCID 516892Sodium BicarbonateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 22557837para-methyl 4-Anilino-1-Boc-piperidineYield 89%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-oxopiperidin-1-carboxylate (5.01 g) and p-toluidine (2.69 g) dissolved in tetrahydrofuran (50 mL) were added sodium triacetoxyborohydride (7.99 g) and then acetic acid (3.0 mL). The reaction solution was stirred for 2 days. The reaction solution was poured into saturated aqueous sodium bicarbonate solution, and it was extracted with ethyl acetate. The extract was washed in turn with water and saturated aqueous sodium chloride solution, and dried (MgSO4). The solvent was distilled off under reduced pressure, and the resulting residue was purified by chromatography (silica gel, 20% ethyl acetate/hexane) to give the title compound (6.49 g).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe extract was washed in turn with water and saturated aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified by chromatography (silica gel, 20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c6f962e8779f4fc3a225207f79f12a70
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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