Ammonia → HCID 21503358, compound

HRID 1287987Notes

Reaction equation

HRID 1287987 reaction equation
[NH2-].[Na+].[F:3][C:4]([F:20])([F:19])[C:5]1[CH:18]=[CH:17][C:16]2[S:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]=2[CH:6]=1.N.Cl[CH2:23][CH:24]1[CH:29]2[CH2:30][CH2:31][N:26]([CH2:27][CH2:28]2)[CH2:25]1>C1(C)C(C)=CC=CC=1.CN(P(N(C)C)(N(C)C)=O)C>[F:20][C:4]([F:3])([F:19])[C:5]1[CH:18]=[CH:17][C:16]2[S:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]([CH2:23][CH:24]3[CH:29]4[CH2:30][CH2:31][N:26]([CH2:27][CH2:28]4)[CH2:25]3)[C:7]=2[CH:6]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 708210H-Phenothiazine, 2-(trifluoromethyl)-HCID 24533Sodium amideHCID 13259909HCID 13259909, compound

Product 1

HCID 21503358HCID 21503358, compound

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolvent3×HCID 12679HexamethylphosphoramideSolvent

Procedure

0.9 ml of a 65% suspension of sodium amide in xylene and then 25 ml of hexamethylphosphotriamide were added to a suspension of 5.3 g of 2-trifluoromethyl-phenothiazine in 25 ml of xylene. The mixture was agitated and heated to reflux. When the evolution of ammonia ceased (2 hours), 16.3 ml of a 9.8% solution of 3-chloromethyl-quinuclidine in xylene were added to the reaction mixture over a period of 30 minutes and refluxing was continued for 18 hours. After cooling, the xylene was evaporated off under reduced pressure and the residual solution was poured into 250 ml of distilled water. The precipitate obtained was separated on Clarcel filter medium, washed with 50 ml of distilled water, and then suspended in 100 ml of ethyl acetate. The insoluble portion was filtered off and the filtrate was washed with 30 ml of distilled water, and then extracted three times with a total of 150 ml of N.aqueous acetic acid. The combined acid extracts were rendered alkaline on an ice bath with 25 ml of ION aqueous sodium carbonate and the oil which separated was extracted twice with a total of 200 ml of ethyl acetate. The combined organic extracts were dried over magnesium sulphate and evaporated. The residue was recrystallised in acetonitrile; 2-trifluoromethyl-10-(3-quinuclidinyl-methyl)-phenothiazine, m.p. 150° C, was obtained.

Workup

  1. temperatureheated to reflux
  2. additionwere added to the reaction mixture over a period of 30 minutes
  3. temperaturerefluxing
  4. temperatureAfter cooling
  5. customthe xylene was evaporated off under reduced pressure
  6. additionthe residual solution was poured into 250 ml of distilled water
  7. customThe precipitate obtained
  8. customwas separated on Clarcel
  9. filtrationfilter medium
  10. washwashed with 50 ml of distilled water
  11. filtrationThe insoluble portion was filtered off
  12. washthe filtrate was washed with 30 ml of distilled water
  13. extractionextracted three times with a total of 150 ml of N.aqueous acetic acid
  14. customthe oil which separated
  15. extractionwas extracted twice with a total of 200 ml of ethyl acetate
  16. dry with materialThe combined organic extracts were dried over magnesium sulphate
  17. customevaporated
  18. customThe residue was recrystallised in acetonitrile

Sources & evidence

ORD record
ord-5a6141971fcd4cc69c4eaf1d4a8b4f19
Source dataset
uspto-grants-1976_10
Patent number
US03987042

Reaction notes

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