Ammonia → HCID 21503359, compound

HRID 1287986Notes

Reaction equation

HRID 1287986 reaction equation
[NH2-].[Na+].[Cl:3][C:4]1[CH:17]=[CH:16][C:15]2[S:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH:5]=1.N.[I-].[K+].Cl[CH2:22][CH:23]1[CH:28]2[CH2:29][CH2:30][N:25]([CH2:26][CH2:27]2)[CH2:24]1>C1(C)C(C)=CC=CC=1.CN(C)C=O>[Cl:3][C:4]1[CH:17]=[CH:16][C:15]2[S:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([CH2:22][CH:23]3[CH:28]4[CH2:29][CH2:30][N:25]([CH2:26][CH2:27]4)[CH2:24]3)[C:6]=2[CH:5]=1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 4875Potassium IodideHCID 70882-ChlorophenothiazineHCID 24533Sodium amideHCID 13259909HCID 13259909, compound

Product 1

HCID 21503359HCID 21503359, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 7237O-XyleneSolvent3×

Procedure

3 ml of a 35% suspension of sodium amide in xylene were added to a suspension of 7 g of 2-chloro-phenothiazine in 100 ml of anhydrous xylene. The mixture was agitated and heated to reflux. When evolution of ammonia ceased (20 hours), a solution of 0.35 g of potassium iodide in 2.3 ml of dimethylformamide was added to the reaction mixture all at once and 34 ml of a 7% solution of 3-chloromethyl-quinuclidine in xylene were then added over a period of an hour. Refluxing of the reaction mixture was continued for 32 hours. After cooling, the reaction mixture was worked up as in Example 2. After recrystallisation of the crude product in in isopropyl oxide, 2-chloro-10-(3-quinuclidinyl-methyl)-phenothiazine, m.p. 122° C, was obtained.

Workup

  1. temperatureheated to reflux
  2. custom(20 hours)
  3. additionwere then added over a period of an hour
  4. temperatureRefluxing of the reaction mixture
  5. temperatureAfter cooling
  6. customAfter recrystallisation of the crude product in in isopropyl oxide, 2-chloro-10-(3-quinuclidinyl-methyl)-phenothiazine, m.p. 122° C
  7. customwas obtained

Sources & evidence

ORD record
ord-31c6566d9ee84a32952f311246bb1acc
Source dataset
uspto-grants-1976_10
Patent number
US03987042

Reaction notes

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