Dichloromethane → 5-(2-Bromoacetylamino)-2,3,4,5-tetrahydro-1-benzoxepine

HRID 953

Reaction equation

HRID 953 reaction equation
C(Cl)Cl.[NH2:4][CH:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[O:9][CH2:8][CH2:7][CH2:6]1.[Br:16][CH2:17][C:18](Br)=[O:19].[Cl-].[NH4+]>C(N(CC)CC)C>[Br:16][CH2:17][C:18]([NH:4][CH:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[O:9][CH2:8][CH2:7][CH2:6]1)=[O:19]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 25517Ammonium ChlorideHCID 61147Bromoacetyl bromideHCID 156196982,3,4,5-Tetrahydro-1-benzoxepin-5-amine

Product 1

HCID 196942705-(2-Bromoacetylamino)-2,3,4,5-tetrahydro-1-benzoxepineYield 65%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a 5 ml methylene chloride solution of 150 mg of 5-amino-2,3,4,5-tetrahydro-1-benzoxepine (Japanese Unexamined Patent Publication (Kokai) No. 4-178381) and 0.15 ml of triethylamine was added dropwise, under ice cooling, 0.08 ml of bromoacetyl bromide. This was then stirred at room temperature for 1 hour. To the reaction was added 5 ml of a saturated aqueous solution of ammonium chloride, then extraction was performed with methylene chloride. The extract was washed with saturated saline, dried, filtered, then concentrated under reduced pressure to obtain a residue which was then purified by silica gel column chromatography (methylene chloride:methanol=25:1) to obtain the above-referenced compound (8) in an amount of 165 mg (yield of 65%).

Workup

  1. extractionextraction
  2. washThe extract was washed with saturated saline
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto obtain a residue which
  7. customwas then purified by silica gel column chromatography (methylene chloride:methanol=25:1)

Sources & evidence

ORD record
ord-a457ce1a504046278989f2096f1b01fc
Source dataset
uspto-grants-1998_03
Patent number
US05723475

Linked notes

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