3-Phenylpropylamine → HCID 178518606, compound

HRID 1007521Notes

Reaction equation

HRID 1007521 reaction equation
[CH:1]1([C:8]2[CH:17]=[CH:16][C:11]3[NH:12][C:13](=[O:15])[O:14][C:10]=3[CH:9]=2)[CH2:6][CH2:5][C:4](=O)[CH2:3][CH2:2]1.[C:18]1([CH2:24][CH2:25][CH2:26][NH2:27])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[BH4-].[Na+]>CC(O)C>[C:18]1([CH2:24][CH2:25][CH2:26][NH:27][C@H:4]2[CH2:5][CH2:6][C@H:1]([C:8]3[CH:17]=[CH:16][C:11]4[NH:12][C:13](=[O:15])[O:14][C:10]=4[CH:9]=3)[CH2:2][CH2:3]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 162593-PhenylpropylamineHCID 4311764Sodium borohydrideHCID 98133826-(4-oxocyclohexyl)-1,3-benzoxazol-2(3H)-one

Product 1

HCID 178518606HCID 178518606, compoundYield 42.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of ketone 5 (0.50 g, 2.0 mmol) in 2-propanol (30 mL) was added 3 Å molecular sieves and 3-phenyl-1-propylamine 10 (0.39 g, 2.0 mmol). The reaction mixture was stirred for 4 hours. Sodium borohydride (0.11 g, 2.83 mmol) was added, and the reaction mixture was stirred overnight, quenched with MeOH, and concentrated under reduced pressure. Purification by flash chromatography (silica, 9.5:5:1 CH2Cl2:MeOH:NH4OH) gave 6-[trans-4-(3-phenylpropylamino)-cyclohexyl]-3H-benzoxazol-2-one (0.30 g, 42%): mp 166-170° C.; IR (KBr): 2933, 1761, 1653, 1582 cm−1; 1H NMR (500 MHz, DMSO-d6): δ 9.09 (s, 1H), 7.30-7.19 (m, 6H), 7.03 (d, J=9 Hz, 1H), 6.68 (d, J=9 Hz, 1H), 2.66 (m, 1H), 2.55 (t, J=8 Hz, 2H), 2.37 (tt, J=10, 2 Hz, 1H), 1.98 (d, J=10 Hz, 1H), 1.96 (d, J=10 Hz, 1H), 1.76 (d, J=3 Hz, 1H), 1.56 (m, 1H), 1.45 (m, 1H), 1.39 (m, 1H), 1.18-1.05 (m, 6H); CI-MS (methane) (m/z): 351 [M+H]+; HRMS-API (m/z): [M+H]+ calcd for C22H26N2O2, 351.2072; found, 351.2178; HPLC: method A, 7.66 minutes (96.9%); method B, 14.14 minutes (97.7%); Anal. Calcd for C22H26N2O2.H2O: C, 71.71; H, 7.66; N, 7.60. Found: C, 71.70; H, 7.62; N, 7.20.

Workup

  1. stirringthe reaction mixture was stirred overnight
  2. customquenched with MeOH
  3. concentrationconcentrated under reduced pressure
  4. customPurification by flash chromatography (silica, 9.5:5:1 CH2Cl2:MeOH:NH4OH)

Sources & evidence

ORD record
ord-875bfb8b957c4d798ca6d1d469b1f547
Source dataset
uspto-grants-2004_09
Patent number
US06794402B2

Reaction notes

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