4-Piperidineethanol → HCID 68127040, compound

HRID 1657591Notes

Reaction equation

HRID 1657591 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][C:11]=3[S:17][CH3:18])[N:6]([CH2:19][CH2:20][CH2:21]Cl)[C:5]=2[CH:4]=1.[OH:23][CH2:24][CH2:25][CH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][C:11]=3[S:17][CH3:18])[N:6]([CH2:19][CH2:20][CH2:21][N:29]3[CH2:30][CH2:31][CH:26]([CH2:25][CH2:24][OH:23])[CH2:27][CH2:28]3)[C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 739534-PiperidineethanolHCID 516892Sodium BicarbonateHCID 21534834HCID 21534834, compound

Product 1

HCID 68127040HCID 68127040, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-methoxy-6-methylthio-10-(3-chloropropyl)phenothiazine (9.2 g.), 4-hydroxyethylpiperidine (3.2 g.) and sodium bicarbonate (8.4 g.) in dimethylformamide (90 cc.) is heated at 120°C., with stirring, for 6 hours. The solvent is then evaporated under reduced pressure (0.1 mm.Hg) at 60°C. The residue is taken up in chloroform (80 cc.) and distilled water (80 cc.) and purification of the product is effected by making the medium acidic and then reprecipitating the base by the procedure mentioned in Example 1. 2-Methoxy-6-methylthio-10-[3-(4-hydroxyethylpiperidino)propyl]-phenothiazine (7.9 g.) in the crude state, in the form of an amorphous beige powder, is thus obtained. This powder is taken up in boiling acetonitrile (15 cc.). After cooling of the solution for 7 hours at a temperature of about 20°C., the crystals which have formed are filtered off, washed with acetonitrile (10 cc.) and with diethyl ether (60 cc.) and then dried at 45°C. under reduced pressure (0.05 mm.Hg) for 17 hours. 2-Methoxy-6-methylthio-10-[3-(4-hydroxyethylpiperidino)propyl]-phenothiazine (7.37 g.), melting at 101°-103°C., is obtained.

Workup

  1. customThe solvent is then evaporated under reduced pressure (0.1 mm.Hg) at 60°C
  2. distillationdistilled
  3. customwater (80 cc.) and purification of the product
  4. customthen reprecipitating the base by the procedure

Sources & evidence

ORD record
ord-fe8e852f3109470d80442e9c730694e8
Source dataset
uspto-grants-1976_06
Patent number
US03961055

Reaction notes

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