Phosphorus oxychloride → HCID 12519138, compound

HRID 2052703Notes

Reaction equation

HRID 2052703 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20][CH2:19]2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=P(Cl)(Cl)[Cl:29]>>[ClH:29].[C:1]1([CH2:7][CH2:8][C:9]2[C:25]3[CH:24]=[CH:23][CH:22]=[C:21]4[C:26]=3[N:18]([CH2:19][CH2:20]4)[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 12519126N-[2-(2,3-Dihydro-1H-indol-1-yl)phenyl]-3-phenylpropanamide

Product 1

HCID 12519138HCID 12519138, compound

Procedure

A rapidly stirred solution of 52.65 g of 1-[2-(3-phenyl-1-oxo-propyl)aminophenyl]indoline in 200 ml POCl3 under N2 is slowly brought to 105°-115° C. After 9.5 hours, the mixture is permitted to cool to room temperature for over 48 hours. The excess POCl3 is distilled at aspirator pressure (bath temperature 55°-60° C.) to yield a solid which is triturated with hexane, filtered, washed with additional hexane, and dried at room temperature under high vacuum to yield 1,2-dihydro-6-(2-phenylethyl)-indolo[1,7-ab][1,5]benzodiazepine hydrochloride, m.p. 181.5°-183.0° C.

Workup

  1. customis slowly brought to 105°-115° C
  2. distillationThe excess POCl3 is distilled at aspirator pressure (bath temperature 55°-60° C.)
  3. customto yield a solid which
  4. customis triturated with hexane
  5. filtrationfiltered
  6. washwashed with additional hexane
  7. customdried at room temperature under high vacuum

Sources & evidence

ORD record
ord-2a176f8d2cd5494b941d2a7b186b4951
Source dataset
uspto-grants-1980_01
Patent number
US04186199

Reaction notes

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