1-Bromo-3-chloropropane → 3-(3-Chloropropyl)-7-methanesulfonyloxy-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 33214Notes

Reaction equation

HRID 33214 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:16]=[CH:15][C:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH2:14][C:8]=2[CH:7]=1)(=[O:4])=[O:3].Br[CH2:18][CH2:19][CH2:20][Cl:21].C(N(CC)CC)C>O1CCCC1>[Cl:21][CH2:20][CH2:19][CH2:18][N:12]1[CH2:11][CH2:10][C:9]2[CH:15]=[CH:16][C:6]([O:5][S:2]([CH3:1])(=[O:3])=[O:4])=[CH:7][C:8]=2[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 8471TriethylamineHCID 112994727-Methanesulfonyloxy-2,3,4,5-tetrahydro-1H-3-benzazepine

Product 1

HCID 865941693-(3-Chloropropyl)-7-methanesulfonyloxy-2,3,4,5-tetrahydro-1H-3-benzazepineYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7-methanesulfonyloxy-2,3,4,5-tetrahydro-1H-3-benzazepine (1.75 g, 7.3 mmol), 1-bromo-3-chloropropane (0.80 ml, 8.1 mmol) and triethylamine (3 ml, 21.5 mmol) in anhydrous tetrahydrofuran (25 ml) was heated at reflux for 5 h. The mixture was cooled, evaporated in vacuo and the residue partitioned between water (100 ml) and ethyl acetate (100 ml). The aqueous layer was extracted with ethyl acetate (100 ml) and the combined organics washed with brine (150 ml), dried (Na2SO4) and evaporated in vacuo. Purification by chromatography on silica gel using 10-70% ethyl acetate in hexane gradient elution gave the title compound as a pale orange oil (1.22 g, 53%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 h
  3. temperatureThe mixture was cooled
  4. customevaporated in vacuo
  5. customthe residue partitioned between water (100 ml) and ethyl acetate (100 ml)
  6. extractionThe aqueous layer was extracted with ethyl acetate (100 ml)
  7. washthe combined organics washed with brine (150 ml)
  8. dry with materialdried (Na2SO4)
  9. customevaporated in vacuo
  10. customPurification by chromatography
  11. washon silica gel using 10-70% ethyl acetate in hexane gradient elution

Sources & evidence

ORD record
ord-262dcd86f3344f1cb62cd95887629c16
Source dataset
uspto-grants-2008_09
Patent number
US07429579B2

Reaction notes

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