4-Piperidineethanol → HCID 21534829, compound

HRID 1657603Notes

Reaction equation

HRID 1657603 reaction equation
[CH2:1]([O:8][C:9]1[CH:22]=[CH:21][C:20]2[S:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[S:23](=[O:28])(=[O:27])[N:24]([CH3:26])[CH3:25])[N:12]([CH2:29][CH2:30][CH2:31]Cl)[C:11]=2[CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[OH:33][CH2:34][CH2:35][CH:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:22]=[CH:21][C:20]2[S:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[S:23](=[O:28])(=[O:27])[N:24]([CH3:26])[CH3:25])[N:12]([CH2:29][CH2:30][CH2:31][N:39]3[CH2:40][CH2:41][CH:36]([CH2:35][CH2:34][OH:33])[CH2:37][CH2:38]3)[C:11]=2[CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 739534-PiperidineethanolHCID 516892Sodium BicarbonateHCID 21534822HCID 21534822, compound

Product 1

HCID 21534829HCID 21534829, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2-heptyloxy-6-dimethylsulphamoyl-10-(3-chloropropyl)phenothiazine (24.3 g.), 4-hydroxyethylpiperidine (7.1 g.) and sodium bicarbonate (16.1 g.) in dimethylformamide (180 cc.) is heated at about 130°C. for 8 hours with stirring. After cooling, the reaction mixture is evaporated to dryness under reduced pressure (15 mm.Hg) with heating to 65°C. The residue is taken up in distilled water (300 cc.) and then extracted with methylene chloride (total 560 cc.). The combined organic extracts are acidified by addition of a solution of methanesulphonic acid (57.6 cc.) in water (250 cc.). The organic phase is washed with an 8% aqueous solution of sodium hydroxide (total 300 cc.) and then with distilled water (total 1 litre), and is finally dried over sodium sulphate. On evaporation of the solvent under reduced pressure (15 mm. Hg) at 40°C., crude 2-heptyloxy-6-dimethylsulphamoyl-10-[3-(4-hydroxyethylpiperidino)propyl]-phenothiazine (21.1 g.), in the form of a brown viscous oil, is obtained.

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture is evaporated to dryness under reduced pressure (15 mm.Hg)
  3. temperaturewith heating to 65°C
  4. extractionextracted with methylene chloride (total 560 cc.)
  5. additionThe combined organic extracts are acidified by addition of a solution of methanesulphonic acid (57.6 cc.) in water (250 cc.)
  6. washThe organic phase is washed with an 8% aqueous solution of sodium hydroxide (total 300 cc.)
  7. dry with materialwith distilled water (total 1 litre), and is finally dried over sodium sulphate
  8. customOn evaporation of the solvent under reduced pressure (15 mm. Hg) at 40°C.

Sources & evidence

ORD record
ord-dddfb84a941548e199e006d8a8c4bd14
Source dataset
uspto-grants-1976_06
Patent number
US03961055

Reaction notes

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