Hydrochloric Acid → Ethyl 4-[bis(phenylmethyl)amino]cyclohexanecarboxylate

HRID 1355587Notes

Reaction equation

HRID 1355587 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.[CH2:13]([NH:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl.[OH-].[Na+]>ClCCCl>[CH2:21]([N:20]([CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7656DibenzylamineHCID 14798Sodium HydroxideHCID 317638Ethyl 4-oxocyclohexanecarboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 22287000Ethyl 4-[bis(phenylmethyl)amino]cyclohexanecarboxylateYield 87.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of ethyl 4-oxocyclohexanecarboxylate (1.9 g, 11 mmol) in 1,2-dichloroethane (113 mL) at 23° C. was added dibenzylamine (3.4 g, 3.3 mL, 17 mmol) in one portion. After 10 min, sodium triacetoxyborohydride (4.81 g, 22.7 mmol) was added, and the resulting cloudy suspension was stirred for 48 hrs. The suspension was poured into 1N aqueous hydrogen chloride (100 mL), the resulting mixture was basified to pH 9.0-10.0 with 12.5 M aqueous sodium hydroxide. The basic layer was extracted with ethyl acetate (3×50 mL), and the combined organic layers were washed with saturated aqueous sodium chloride (70 mL), dried over sodium sulfate, and concentrated in vacuo. The resulting residue was purified by flash chromatography (5-10% ethyl acetate in hexanes) to yield ethyl 4-(N,N-dibenzylamino)cyclohexanecarboxylate (3.4 g, 84%) as a clear oil. MS (ESI) 352 (M+H).

Workup

  1. extractionThe basic layer was extracted with ethyl acetate (3×50 mL)
  2. washthe combined organic layers were washed with saturated aqueous sodium chloride (70 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by flash chromatography (5-10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-dafe6227b9424079a0dd7cc7b28e2328
Source dataset
uspto-grants-2003_07
Patent number
US06586446B1

Reaction notes

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