Pyrrolidine → 7-chloro-10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbonitrile

HRID 704224Notes

Reaction equation

HRID 704224 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.CS(O[CH2:11][CH:12]([N:14]1[C:27]2[CH:26]=[C:25]([C:28]#[N:29])[CH:24]=[CH:23][C:22]=2[S:21][C:20]2[C:15]1=[CH:16][CH:17]=[C:18]([Cl:30])[CH:19]=2)[CH3:13])(=O)=O>C1(C)C=CC=CC=1>[Cl:30][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH:12]([CH3:13])[CH2:11][N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)[C:27]1[CH:26]=[C:25]([C:28]#[N:29])[CH:24]=[CH:23][C:22]=1[S:21]2

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 15925250(2RS)-2-(7-chloro-2-cyano-10-phenothiazinyl)propyl methanesulphonate

Product 1

HCID 159253667-chloro-10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Pyrrolidine (21.1 cc) is added to a suspension of (2RS)-2-(7-chloro-2-cyano-10-phenothiazinyl)propyl methanesulphonate (72.1 g) in toluene (166 cc). The mixture is brought to 120° C. for 21 hours, and then to 150° C. for 12 hours. After cooling, the mixture is washed with distilled water (5×250 cc). The organic phase is dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) to give 7-chloro-10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbonitrile (19.2 g).

Workup

  1. waitto 150° C. for 12 hours
  2. temperatureAfter cooling
  3. washthe mixture is washed with distilled water (5×250 cc)
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa)

Sources & evidence

ORD record
ord-0f644bf331754bae8253500e3e7b110c
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

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