chloroform methanol HOAc → HCID 131715558, compound

HRID 1253306Notes

Reaction equation

HRID 1253306 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]2[CH2:32][CH2:31][CH2:30][CH2:29]2)[C:4]1=[O:33].C(Cl)(Cl)[Cl:35].CO.[C:40](O)(=[O:42])[CH3:41]>C(OC(=O)C)(=O)C>[ClH:35].[C:40]([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:24])([F:23])[F:25])[CH:20]=[CH:21][C:6]=2[N:5]([CH2:26][CH2:27][N:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)[C:4]1=[O:33])(=[O:42])[CH3:41]

Participants

4

Reactant 2

HCID 21866353chloroform methanol HOAcHCID 131715559HCID 131715559, compound

Product 1

HCID 131715558HCID 131715558, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A stirred solution of (cis)-3-hydroxy-1-[2-(1-pyrrolidinyl)ethyl]-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-7-(trifluoromethyl)-2H-1-benzazepin-2-one, monohydrochloride (3.3 g, 0.0056 mmol) in 80 ml of acetic anhydride under argon was heated in an oil bath at 114°-119° C. for 4.5 hours. The bulk of acetic anhydride was removed on a rotary evaporator at 0.2 mm and the solid residue (12 g) was suspended in 30 ml of ethyl acetate, diluted with 60 ml of ether, cooled for 1 hour, filtered, washed with ether, and dried in vacuo overnight; yield, 2.60 g; melting point 228°-230° C. (dec.); s, 225° C. TLC: Rf =0.48 (8:1:1, chloroform-methanol-acetic acid).

Workup

  1. customThe bulk of acetic anhydride was removed on a rotary evaporator at 0.2 mm
  2. additiondiluted with 60 ml of ether
  3. temperaturecooled for 1 hour
  4. filtrationfiltered
  5. washwashed with ether
  6. customdried in vacuo overnight
  7. customyield
  8. customs, 225° C

Sources & evidence

ORD record
ord-60ba5f398b29454ca1a828ef713ec6b4
Source dataset
uspto-grants-1988_05
Patent number
US04748239

Reaction notes

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