Acetic Acid → HCID 20343914, compound

HRID 2049643Notes

Reaction equation

HRID 2049643 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[O:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:13]3([C:21](=[O:22])[C:4]=2[CH:3]=1)[CH2:18][CH2:17][N:16](C#N)[CH2:15][CH2:14]3.C(O)(=O)C.[BrH:29]>Cl.O.CCOCC>[BrH:29].[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[O:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:13]3([C:21](=[O:22])[C:4]=2[CH:3]=1)[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]3

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 20343909HCID 20343909, compound

Product 1

HCID 20343914HCID 20343914, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A homogeneous solution of 1.8 g of 2-chloro-1'-cyano-10,11-dihydro-11-oxospiro[dibenz(b,f)oxepin-10,4'-piperidine], Example 4, in 20 ml of 3 N hydrochloric acid and 10 ml of glacial acetic acid is stirred at 110°-120° C. for 16 hours and then the solution is permitted to cool to ambient temperature. Thereafter, the solution is diluted with 50 ml of water and then is rotary evaporated at 80° C. until 50 ml of water is removed and the dilution and evaporation process is repeated. The residue is diluted with 200 ml of water and the diluted solution is successively cooled in an ice bath, basified to pH 9 with a small amount of 58% ammonium hydroxide and extracted thrice with 80 ml portions of ether. The combined ether extracts are sequentially washed twice with two 80 ml portions of water and one 40 ml portion of saturated sodium chloride and then dried over magnesium sulfate and finally evaporated to dryness leaving an oil. The oil is dissolved in ether where it is converted to its hydrobromic acid salt. The salt is recrystallized from acetone to provide crystals of 2-chloro-10,11-dihydro-11-oxospiro[dibenz(b,f)oxepin-10,4'-piperidine]hydrobromide which lose their regular shape upon heating above 125° C. and the resulting glass melts at 223°-225° C.

Workup

  1. customis rotary evaporated at 80° C. until 50 ml of water
  2. customis removed
  3. customthe dilution and evaporation process
  4. additionThe residue is diluted with 200 ml of water
  5. temperaturethe diluted solution is successively cooled in an ice bath
  6. extractionextracted thrice with 80 ml portions of ether
  7. washThe combined ether extracts are sequentially washed twice with two 80 ml portions of water and one 40 ml portion of saturated sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. customfinally evaporated to dryness
  10. customleaving an oil
  11. customThe salt is recrystallized from acetone

Sources & evidence

ORD record
ord-5ce62f78367d41159ee37ef27b4ed0e5
Source dataset
uspto-grants-1980_04
Patent number
US04198418

Reaction notes

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