Benzophenone → HCID 45275495, compound

HRID 1667165Notes

Reaction equation

HRID 1667165 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8](=[O:29])[CH2:9][N:10]2[CH2:15][CH2:14][CH2:13][C:12]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:11]2=[O:28])[CH2:4][CH2:3]1.[C:30]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)(=O)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[BH4-].[Na+]>ClCCl.CO.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH:30]([NH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8](=[O:29])[CH2:9][N:10]2[CH2:15][CH2:14][CH2:13][C:12]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:11]2=[O:28])[CH2:4][CH2:3]1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

7

Reactant 3

HCID 3102BenzophenoneHCID 4311764Sodium borohydrideHCID 673590361-(2-(4-Aminopiperidin-1-yl)-2-oxoethyl)-3,3-diphenylpiperidin-2-one

Product 1

HCID 45275495HCID 45275495, compound

Reagents, catalysts & solvents 3

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(2-(4-aminopiperidin-1-yl)-2-oxoethyl)-3,3-diphenylpiperidin-2-one (Example 87B, 0.1 g, 0.25 mmol) and benzophenone (0.056 g, 0.3 mmol) is stirred in dichloromethane (3 mL) with titanium(IV) isopropoxide (0.012 g, 0.4 mmol) for 3 hours. The reaction mixture was then diluted with methanol (10 mL) and sodium borohydride (0.4 g, 0.4 mmol) was added. The mixture was stirred at ambient temperature for 16 hours and then concentrated. The residue was partition in ethyl acetate/H2O (100 mL/20 mL). The organic layer was dried over MgSO4 and concentrated. The residue was chromatographed on silica gel eluting with 5-10% methanol/dichloromethane. 1H NMR (300 MHz, CDCl3) δ ppm 7.26-7.38 (m, 16H), 7.15-7.24 (m, 4H), 4.99 (s, 1H), 4.36-4.44 (m, 1H), 4.21 (s, 2H), 3.70-3.77 (m, 1H), 3.48 (t, J=6.4 Hz, 2H), 2.93-3.03 (m, 1H), 2.69-2.79 (m, 1H), 2.61-2.69 (m, 3H), 1.89-2.00 (m, 2H), 1.77-1.89 (m, 2H), 1.24-1.41 (m, 3H); MS (ESI+) m/z 558 (M+H)+.

Workup

  1. additionwas added
  2. concentrationconcentrated
  3. customThe residue was partition in ethyl acetate/H2O (100 mL/20 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel eluting with 5-10% methanol/dichloromethane

Sources & evidence

ORD record
ord-5af95f79a713405784e4d45981b8d43f
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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