Acetyl bromide → 3-cyclopropylmethyl-6-chloro-7,8-diacetoxy-1-(p-acetoxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine hydrobromide

HRID 1065027Notes

Reaction equation

HRID 1065027 reaction equation
Br.[CH:2]1([CH2:5][N:6]2[CH2:12][CH:11]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)[C:10]3[CH:20]=[C:21]([OH:26])[C:22]([OH:25])=[C:23]([Cl:24])[C:9]=3[CH2:8][CH2:7]2)[CH2:4][CH2:3]1.[C:27]([Br:30])(=[O:29])[CH3:28]>FC(F)(F)C(O)=O>[BrH:30].[CH:2]1([CH2:5][N:6]2[CH2:12][CH:11]([C:13]3[CH:14]=[CH:15][C:16]([O:19][C:27](=[O:29])[CH3:28])=[CH:17][CH:18]=3)[C:10]3[CH:20]=[C:21]([O:26][C:22](=[O:25])[CH3:21])[C:22]([O:25][C:16](=[O:19])[CH3:15])=[C:23]([Cl:24])[C:9]=3[CH2:8][CH2:7]2)[CH2:3][CH2:4]1

Participants

4

Reactant 2

HCID 10482Acetyl bromideHCID 20541082HCID 20541082, compound

Product 1

HCID 205410803-cyclopropylmethyl-6-chloro-7,8-diacetoxy-1-(p-acetoxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine hydrobromide

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 1 g of 3-cyclopropylmethyl-6-chloro-7,8-dihydroxy-1-(p-hydroxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine hydrobromide, 1.3 ml of acetyl bromide and 200 ml of trifluoroacetic acid is heated at reflux for 2 hours. After evaporation to dryness, the residue is purified, if necessary, by recrystallization to give 3-cyclopropylmethyl-6-chloro-7,8-diacetoxy-1-(p-acetoxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine hydrobromide. Similarly tri-isobutyryloxy, -propionyloxy, -isovaleryloxy, -n-butyryloxy and -n-heptanoyloxy ester derivatives are prepared.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 2 hours
  3. customAfter evaporation to dryness
  4. customthe residue is purified
  5. customif necessary, by recrystallization

Sources & evidence

ORD record
ord-4fb3e72eaeaa4206a7efdb18c1d3301d
Source dataset
uspto-grants-1982_05
Patent number
US04328153

Reaction notes

Loading…