Acetone → HCID 178457163, compound

HRID 896645Notes

Reaction equation

HRID 896645 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][NH:10][C@H:11]2[CH2:16][CH2:15][C@H:14]([C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:24][C:25]([CH3:27])=O.C1COCC1.C([BH3-])#N.[Na+]>C(O)(=O)C.CO>[CH:25]([N:10]([C@H:11]1[CH2:12][CH2:13][C@H:14]([C:17]2[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=2)[CH2:15][CH2:16]1)[CH2:9][CH2:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([CH3:27])[CH3:24]

Participants

7

Reactant 4

HCID 180AcetoneHCID 8028TetrahydrofuranHCID 5003444Sodium cyanoborohydrideHCID 178516054HCID 178516054, compound

Product 1

HCID 178457163HCID 178457163, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of trans-4-[4-(3-phenylpropyl amino) cyclohexyl]-phenol and acetone (2 mL) in a 2:1 mixture of THF:MeOH (10 mL) was added sodium cyanoborohydride (153 mg, 2.42 mmol). The reaction mixture was heated to 60° C. and the acidity was maintained by the addition of acetic acid. The mixture was stirred overnight, quenched with 2N NaOH and concentrated under reduced pressure. Purification by flash chromatography (90:9:1 CH2Cl2:MeOH:NH4OH) gave trans-4-{4-[N-isopropyl-N-(3-phenylpropyl) amino]cyclohexyl}phenol (130 mg, 48%), as a white solid: mp 146-154° C.; IR (KBr): 3198, 2941, 1613 cm−1; 1H NMR (500 MHz, DMSO-d6) δ or s δ 7.32-7.21 (m, 5H), 6.98 (d, J=8 Hz, 2H), 6.66 (d, J=8 Hz, 2H), 3.67 (m, 1H), 3.28 (m, 2H), 3.10 (m, 2H), 2.66 (m, 2H), 2.48 (m, 1H), 2.04 (m, 1H), 2.02 (m, 2H), 1.84 (m, 2H), 1.83 (m, 2H), 1.49 (m, 2H), 1.24 (d, J=8 Hz, 3H), 1.19 (d, J=8 Hz, 3H); CI-MS (methane) (m/z): 352 [M+H]+; HRMS-API (m/z): [M+H]+ Calcd for C24H33NO, 352.2640. found: 352.2637. HPLC: method A, 6.37 minutes (95.3%); method B, 10.85 minutes (100%); Anal. Calcd for C24H33NO.HCl.0.5 NaCl: C, 69.09; H, 8.21; N, 3.36. Found: C, 69.33; H, 8.32; N, 3.22.

Workup

  1. customquenched with 2N NaOH
  2. concentrationconcentrated under reduced pressure
  3. customPurification by flash chromatography (90:9:1 CH2Cl2:MeOH:NH4OH)

Sources & evidence

ORD record
ord-cad2a64c135247438900b9dfba0ad30d
Source dataset
uspto-grants-2005_07
Patent number
US06919377B2

Reaction notes

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