Hydrochloric Acid → Ethanol, 2-((1-(3-(10H-phenothiazin-10-yl)propyl)-4-piperidinyl)oxy)-, monohydrochloride

HRID 329036Notes

Reaction equation

HRID 329036 reaction equation
[I-].[Na+].[Cl:3][CH2:4][CH2:5][CH2:6][N:7]1[C:20]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[S:14][C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2.C(N(CC)CC)C.[NH:28]1[CH2:33][CH2:32][CH:31]([O:34][CH2:35][CH2:36][OH:37])[CH2:30][CH2:29]1.Cl>C(C(C)=O)C.CCOCC>[ClH:3].[OH:37][CH2:36][CH2:35][O:34][CH:31]1[CH2:32][CH2:33][N:28]([CH2:4][CH2:5][CH2:6][N:7]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[S:14][C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:29][CH2:30]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 8471TriethylamineHCID 1229912010-(3-chloropropyl)-10H-phenothiazineHCID 202953322-(Piperidin-4-yloxy)ethan-1-ol

Product 1

HCID 218308Ethanol, 2-((1-(3-(10H-phenothiazin-10-yl)propyl)-4-piperidinyl)oxy)-, monohydrochlorideYield 55.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6569Methyl Ethyl KetoneSolvent

Procedure

22.5 g (0.15 mole) of sodium iodide was added to a solution of 41.5 g (0.15 mole) of 10-(3-chloropropyl)-phenothiazine in 400 ml of methyl ethyl ketone and then 15.2 g (0.15 mole) of triethylamine followed by 21.7 g (0.15 mole) of 2-(4-piperidyloxy)-ethanol were added to the reaction mixture. The solution was refluxed with stirring for 20 hours and after cooling, the precipitate formed was removed by vacuum filtration. The filtrate was evaporated to dryness and the oily residue was extracted with aqueous hydrochloric acid. The acidic extract was washed with ether, made alkaline and was extracted with benzene. The benzene phase was repeatedly washed with water, dried and concentrated to obtain an oil. The oil was dissolved in ether and hydrogen chloride in ether was added thereto. The precipitate was recoved by vacuum filtration and was crystallized from a 95% ethanol-ether mixture to obtain 35 g (55% yield) of 10-[3-(4-β-hydroxyethoxypiperidino)-propyl]-phenothiazine hydrochloride in the form of white crystals melting at 183° C on a heated microscopic stage. The product was identical to that of Example XI.

Workup

  1. additionwere added to the reaction mixture
  2. temperatureThe solution was refluxed
  3. temperatureafter cooling
  4. customthe precipitate formed
  5. customwas removed by vacuum filtration
  6. customThe filtrate was evaporated to dryness
  7. extractionthe oily residue was extracted with aqueous hydrochloric acid
  8. extractionThe acidic extract
  9. washwas washed with ether
  10. extractionwas extracted with benzene
  11. washThe benzene phase was repeatedly washed with water
  12. customdried
  13. concentrationconcentrated
  14. customto obtain an oil
  15. filtrationThe precipitate was recoved by vacuum filtration
  16. customwas crystallized from a 95% ethanol-ether mixture

Sources & evidence

ORD record
ord-f0f9e570c2f94fb292e7991327982bb8
Source dataset
uspto-grants-1977_04
Patent number
US04018922

Reaction notes

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