Cyclohexane, (bromomethyl)- → N-[(1-Cyclohexylmethyl-4-piperidyl)methyl] 3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxamide

HRID 609598Notes

Reaction equation

HRID 609598 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9]([C:11]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]3[CH2:20][CH2:21][CH2:22][O:23][C:12]=23)=[O:10])[CH2:3][CH2:2]1.[CH:24]1([CH2:30]Br)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>>[CH:24]1([CH2:30][N:1]2[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9]([C:11]3[C:19]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[N:13]4[CH2:20][CH2:21][CH2:22][O:23][C:12]=34)=[O:10])[CH2:3][CH2:2]2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

3

Reactant 2

HCID 137636Cyclohexane, (bromomethyl)-HCID 9839803N-(4-Piperidylmethyl) 3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxamide

Product 1

HCID 19599430N-[(1-Cyclohexylmethyl-4-piperidyl)methyl] 3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxamide

Procedure

N-(4-Piperidylmethyl) 3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxamide (E21) was alkylated with cyclohexylmethyl bromide using the method of Example 22 with a reaction time of 70 h at room temperature followed by 8 h at reflux temperature. The title compound (E23) was obtained as a white solid (31%) which was converted to its hydrochloride salt and crystallised from acetone/ether as a white solid mp 209-210° C.

Workup

  1. customwith a reaction time of 70 h
  2. customat room temperature
  3. temperatureat reflux temperature

Sources & evidence

ORD record
ord-be72e82c748c4a63a48e064a2ee2236f
Source dataset
uspto-grants-1999_12
Patent number
US05998409

Reaction notes

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