Hydrochloric Acid → (cis)-3-(Acetyloxy)-1-[2-(dimethylamino)ethyl]-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-7-(trifluoromethyl)-2H-1-benzazepin-2-one, monohydrochloride

HRID 1253304Notes

Reaction equation

HRID 1253304 reaction equation
Cl.[OH:2][C@H:3]1[C@@H:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH2:8][C:7]2[CH:18]=[C:19]([C:22]([F:25])([F:24])[F:23])[CH:20]=[CH:21][C:6]=2[N:5]([CH2:26][CH2:27][N:28]([CH3:30])[CH3:29])[C:4]1=[O:31].[Cl:32]CCl.CO.[C:37](O)(=[O:39])[CH3:38].Cl>C(OC(=O)C)(=O)C.CCOCC>[ClH:32].[C:37]([O:2][C@H:3]1[C@@H:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH2:8][C:7]2[CH:18]=[C:19]([C:22]([F:23])([F:25])[F:24])[CH:20]=[CH:21][C:6]=2[N:5]([CH2:26][CH2:27][N:28]([CH3:30])[CH3:29])[C:4]1=[O:31])(=[O:39])[CH3:38]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21877243DCM MeOH AcOHHCID 131715557(cis)-3-(Hydroxy)-1-[2-(dimethylamino)ethyl]-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-7-(trifluormethyl)-2H-1-benzazepin-2-one, monohydrochloride

Product 1

HCID 49861173(cis)-3-(Acetyloxy)-1-[2-(dimethylamino)ethyl]-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-7-(trifluoromethyl)-2H-1-benzazepin-2-one, monohydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 7918Acetic AnhydrideSolvent

Procedure

A stirred suspension of (cis)-3-(hydroxy)-1-[2-(dimethylamino)ethyl]-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-7-(trifluoromethyl)-2H-1-benzazepin-2-one, monohydrochloride (1.50 g; 3.27 mmol) in 50 ml of acetic anhydride was heated in an oil bath at 110°-117° C. (solution obtained) for 2.5 hours (under argon). TLC (8:1:1 dichloromethane-methanol-acetic acid) showed the reaction to be complete. The acetic anhydride was removed on a rotary evaporator at 0.2 mm to give a solid. The latter was rubbed under ethyl acetate, 1 ml of saturated hydrogen chloride in ether (to pH 2) was added and the evaporation repeated. The colorless material was rubbed under ether, cooled overnight, filtered, washed in ether, and dried in vacuo; yield 1.43 g; melting point 230°-232° C. (dec.); s. 227° C. TLC: Rf =0.41 (8:1:1 dichloromethane-methanol-acetic acid).

Workup

  1. temperaturewas heated in an oil bath at 110°-117° C.
  2. custom(solution obtained) for 2.5 hours (under argon)
  3. customthe reaction
  4. customThe acetic anhydride was removed on a rotary evaporator at 0.2 mm
  5. customto give a solid
  6. customthe evaporation
  7. temperaturecooled overnight
  8. filtrationfiltered
  9. washwashed in ether
  10. customdried in vacuo
  11. custom227° C

Sources & evidence

ORD record
ord-a278f0beb89f4fc187306a7b930808ac
Source dataset
uspto-grants-1988_05
Patent number
US04748239

Reaction notes

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