Sodium borohydride → HCID 178518613, compound

HRID 1007553

Reaction equation

HRID 1007553 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:17]=[CH:16][C:11]3[NH:12][C:13](=[O:15])[S:14][C:10]=3[CH:9]=2)[CH2:4][CH2:3]1.[F:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH2:27][NH2:28])=[CH:21][CH:20]=1.[BH4-].[Na+]>CC(O)C>[F:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:25][CH2:26][CH2:27][NH:28][C@H:2]2[CH2:7][CH2:6][C@H:5]([C:8]3[CH:17]=[CH:16][C:11]4[NH:12][C:13](=[O:15])[S:14][C:10]=4[CH:9]=3)[CH2:4][CH2:3]2)=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 64837963-(4-Fluorophenyl)propan-1-amineHCID 226691096-(4-oxocyclohexyl)-3H-benzothiazol-2-one

Product 1

HCID 178518613HCID 178518613, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of ketone 25 (2.3 g, 9.3 mmol) in 2-propanol (30 mL) was added 4 Å molecular sieves and 3-(4-fluorophenyl)-1-propylamine (1.76 g, 9.3 mmol). The reaction mixture was stirred for 4 hours. Sodium borohydride (0.49 g, 13.03 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-(4-fluorophenyl)propylamino]cyclohexyl}-3H-benzthiazol-2-one (0.24 g, 7%): 1H NMR (500 MHz, DMSO-d6): δ 7.39 (s, 1H), 7.25-7.06 (m, 6H), 3.01 (m, 1H), 2.86 (t, J=8 Hz, 2H), 2.61 (t, J=8 Hz, 2H), 2.37 (m, 1H), 2.01 (m, 2H), 1.92-1.81 (m, 4H), 1.49-1.36 (m, 4H).

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-38016c99bab84550bd3cf33a66b347a3
Source dataset
uspto-grants-2004_09
Patent number
US06794402B2

Linked notes

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