1-Bromo-3-chloropropane → 3-(3-chloropropyl)-7-(1,3-dimethyl-1H-pyrazol-5-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 1674499Notes

Reaction equation

HRID 1674499 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:17]=[CH:16][C:10]3[CH2:11][CH2:12][NH:13][CH2:14][CH2:15][C:9]=3[CH:8]=2)=[CH:5][C:4]([CH3:18])=[N:3]1.Br[CH2:20][CH2:21][CH2:22][Cl:23]>C1COCC1.C(N(C(C)C)CC)(C)C.C(OCC)(=O)C>[Cl:23][CH2:22][CH2:21][CH2:20][N:13]1[CH2:12][CH2:11][C:10]2[CH:16]=[CH:17][C:7]([C:6]3[N:2]([CH3:1])[N:3]=[C:4]([CH3:18])[CH:5]=3)=[CH:8][C:9]=2[CH2:15][CH2:14]1

Participants

6

Reactant 2

HCID 80061-Bromo-3-chloropropaneHCID 251050497-(1,3-Dimethyl-1H-pyrazol-5-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine

Product 1

HCID 598642723-(3-chloropropyl)-7-(1,3-dimethyl-1H-pyrazol-5-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 81531DiisopropylethylamineSolvent

Procedure

To a solution of 7-(1,3-dimethyl-1H-pyrazol-5-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine (0.5 g) in dry THF (10 ml), diisopropylethylamine (0.85 ml) and 1-bromo-3-chloropropane (0.47 mL) were added and the resulting mixture was refluxed for 7 hours. After cooling at room temperature it was diluted with ethyl acetate (30 ml) washed twice with a saturated solution of NaHCO3 in water (20 ml), dried over Na2SO4 and concentrated under reduced pressure. The crude was purified by biotage chromatography using a silica 25 M+ cartridge and eluting with cHex/EtOAc 8:2 to give the title compound as a colourless oil (0.57 g).

Workup

  1. temperaturethe resulting mixture was refluxed for 7 hours
  2. washwashed twice with a saturated solution of NaHCO3 in water (20 ml)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude was purified by biotage chromatography
  6. washeluting with cHex/EtOAc 8:2

Sources & evidence

ORD record
ord-9e4425278d444a35bfef2fb70b79198c
Source dataset
uspto-grants-2011_08
Patent number
US08003638B2

Reaction notes

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