Hydrochloric Acid → HCID 131715560, compound

HRID 1253307Notes

Reaction equation

HRID 1253307 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]([Cl:22])[CH:20]=[CH:21][C:6]=2[N:5]([CH2:23][CH2:24][CH2:25][N:26]([CH3:28])[CH3:27])[C:4]1=[O:29].Cl.ClCCl.CO.[C:36](O)(=[O:38])[CH3:37]>C(OC(=O)C)(=O)C.CCOCC>[ClH:22].[C:36]([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]([Cl:22])[CH:20]=[CH:21][C:6]=2[N:5]([CH2:23][CH2:24][CH2:25][N:26]([CH3:27])[CH3:28])[C:4]1=[O:29])(=[O:38])[CH3:37]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21877243DCM MeOH AcOHHCID 131715561HCID 131715561, compound

Product 1

HCID 131715560HCID 131715560, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 7918Acetic AnhydrideSolvent

Procedure

A stirred suspension of (cis)-3-(hydroxy)-7-chloro-1-[3-(dimethylamino)propyl]-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one, monohydrochloride (0.96 g; 2.18 mmol) in 35 ml of acetic anhydride was heated in an oil bath under argon and the resulting solution kept at 115°-118,° C. for 3 hours. The acetic anhydride was removed on a rotary evaporator at 0.2 mm to give a solid. The latter was rubbed under ethyl acetate, treated with 0.5 ml of saturated hydrogen chloride in ether to pH 2 and the evaporation repeated. The solid was rubbed under ether, evaporated, and pump-dried. The colorless material was rubbed under fresh ether, cooled overnight, filtered, washed with ether, and dried in vacuo; yield, 0.96 g; melting point 212°-215° C. (dec.), s, 200° C. TLC: Rf =0.32 (8:1:1, dichloromethane-methanol-acetic acid).

Workup

  1. temperaturewas heated in an oil bath under argon
  2. customkept at 115°
  3. customThe acetic anhydride was removed on a rotary evaporator at 0.2 mm
  4. customto give a solid
  5. customthe evaporation
  6. customevaporated
  7. custompump-dried
  8. temperaturecooled overnight
  9. filtrationfiltered
  10. washwashed with ether
  11. customdried in vacuo
  12. customyield
  13. customs, 200° C

Sources & evidence

ORD record
ord-0508e288023c44ed896ba97d20123190
Source dataset
uspto-grants-1988_05
Patent number
US04748239

Reaction notes

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