Water → HCID 21390562, compound

HRID 462109Notes

Reaction equation

HRID 462109 reaction equation
[H-].[Na+].Cl.[CH2:4]1[O:17][C:16]2[C:6](=[CH:7][C:8]3[CH2:14][CH2:13][NH:12][CH2:11][CH2:10][C:9]=3[CH:15]=2)[O:5]1.[F:18][C:19]1[CH:30]=[CH:29][C:22]([C:23]([CH2:25][CH2:26][CH2:27][Cl:28])=[O:24])=[CH:21][CH:20]=1.O>CN(C=O)C>[ClH:28].[F:18][C:19]1[CH:20]=[CH:21][C:22]([C:23]([CH2:25][CH2:26][CH2:27][N:12]2[CH2:13][CH2:14][C:8]3[CH:7]=[C:6]4[O:5][CH2:4][O:17][C:16]4=[CH:15][C:9]=3[CH2:10][CH2:11]2)=[O:24])=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 962WaterHCID 197503-(4-Fluorobenzoyl)propyl chlorideHCID 24758Sodium hydrideHCID 22003877HCID 22003877, compound

Product 1

HCID 21390562HCID 21390562, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The sodium hydride obtained by washing 1.95 g of the 54% dispersion (0.042 moles) with benzene was used to prepare the sodium salt from 4.54 g. of 2,3,4,5-tetrahydro-7,8-methylenedioxy-1H-3-benzazepine hydrochloride in 50 ml of DMF as described in Example 35. Treatment of the suspension with 4.41 g of 3-(4-fluorobenzoyl)propyl chloride (0.022 moles) for 24 hours at 55°-60° followed by decomposition with 200 ml of ice water gave an oil-water suspension. The base was recovered by extraction with benzene (3 × 50 ml), the combined extracts washed once with water, then dried, and the solvent distilled in the rotary evaporator. To the residual oil, 3N hydrochloric acid was added and the mixture digested for an hour. After cooling the salt was filtered off, mp 195°14 197°. Two further recrystallizations from water gave the above-named product as a buff colored salt, mp 209°-210°.

Workup

  1. washby washing 1.95 g of the 54% dispersion (0.042 moles) with benzene
  2. customto prepare the sodium salt from 4.54 g
  3. customThe base was recovered by extraction with benzene (3 × 50 ml)
  4. washthe combined extracts washed once with water
  5. customdried
  6. distillationthe solvent distilled in the rotary evaporator
  7. additionTo the residual oil, 3N hydrochloric acid was added
  8. waitthe mixture digested for an hour
  9. temperatureAfter cooling the salt
  10. filtrationwas filtered off
  11. custommp 195°14 197°
  12. customTwo further recrystallizations from water
  13. customgave the above-named product as a buff colored salt, mp 209°-210°

Sources & evidence

ORD record
ord-f5367667fb5f401898de1fa3c74b5b24
Source dataset
uspto-grants-1977_12
Patent number
US04065473

Reaction notes

Loading…