Benzhydrylamine → HCID 178420362, compound

HRID 1497016Notes

Reaction equation

HRID 1497016 reaction equation
[CH:1]([NH:14][C@H:15]1[CH2:20][CH2:19][C@@H:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:17][CH2:16]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C2CCC(=O)CC2)C=CC=CC=1.C1(C(C2C=CC=CC=2)N)C=CC=CC=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH:1]([NH:14][C@H:15]1[CH2:16][CH2:17][C@H:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:19][CH2:20]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 7036BenzhydrylamineHCID 786054-PhenylcyclohexanoneHCID 5049666Sodium triacetoxyborohydrideHCID 178420361HCID 178420361, compound

Product 1

HCID 178420362HCID 178420362, compoundYield 19.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Cis-N-benzhydryl-4-phenylcyclohexanamine: To a solution of 4-phenylcyclohexanone (500 mg, 2.87 mmol) and diphenylmethanamine (526 mg, 2.87 mmol) in DCE (4 mL) at 0° C. was added sodium triacetoxyborohydride (912 mg, 4.30 mmol) by portions slowly. A white suspension resulted and was stirred for 5 min before the ice-water bath was removed. The reaction was stirred at rt for 1.5 h. The reaction was quenched with water carefully, then saturated NaHCO3 was added carefully and the aqueous portion was extracted with DCM (3×). The organic layers were combined, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (0-100% hexane/EtOAc) to give Intermediate 1A (734 mg, 2.15 mmol, 74.9% yield) and trans-N-benzhydryl-4-phenylcyclohexanamine (191 mg, 0.559 mmol, 19.5% yield), LC-MS (ESI) m/z 342.1 (M+H), RT=1.76 min (Method B). 1H NMR (400 MHz, chloroform-d) δ ppm 7.37 (4H, d, J=7.33 Hz), 7.23-7.31 (6H, m), 7.11-7.23 (5H, m), 4.91 (1H, s), 2.80-2.88 (1H, m), 2.46-2.56 (1H, m), 1.74-1.90 (4H, m), 1.60-1.70 (2H, m), 1.47-1.59 (2H, m).

Workup

  1. customA white suspension resulted
  2. customwas removed
  3. customThe reaction was quenched with water carefully
  4. additionsaturated NaHCO3 was added carefully
  5. extractionthe aqueous portion was extracted with DCM (3×)
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by flash chromatography (0-100% hexane/EtOAc)

Sources & evidence

ORD record
ord-07737179994a439cb7a021a459fab6cd
Source dataset
uspto-grants-2015_12
Patent number
US09199946B2

Reaction notes

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