1-Bromopropane → N-benzyl-(3-isopropoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine

HRID 2299615Notes

Reaction equation

HRID 2299615 reaction equation
[H-].[Na+].[CH2:3]([NH:10][CH:11]1[CH2:17][C:16]2[CH:18]=[C:19]([OH:22])[CH:20]=[CH:21][C:15]=2[CH2:14][CH2:13][CH2:12]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:23][CH2:24][CH2:25]Br.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH2:3]([NH:10][CH:11]1[CH2:12][CH2:13][CH2:14][C:15]2[CH:21]=[CH:20][C:19]([O:22][CH:24]([CH3:25])[CH3:23])=[CH:18][C:16]=2[CH2:17]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 18007284HCID 18007284, compound

Product 1

HCID 18007411N-benzyl-(3-isopropoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under nitrogen, to a suspension of sodium hydride (60% in oil, 47 mg) in N,N-dimethylformamide (3 ml) was dropwise added 8-benzylamino-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ol (300 mg) in N,N-dimethylformamide (2 ml) at 5° C., and the mixture was stirred at the same temperature for 30 minutes. To this one was added n-propyl bromide (0.10 ml), and the mixture was stirred at the same temperature for 3 hours. The resulting mixture was poured into saturated aqueous sodium hydrogencarbonate, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate =50:1 to 30:1) to give N-benzyl-(3-isopropoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine (278 mg)

Workup

  1. customat 5° C.
  2. stirringthe mixture was stirred at the same temperature for 3 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate =50:1 to 30:1)

Sources & evidence

ORD record
ord-406d3183159f4824a1a4fe25bab15c8d
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

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