Cysteamine → HCID 18915889, compound

HRID 1379622Notes

Reaction equation

HRID 1379622 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH2:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH2:20][C:21](Cl)=[O:22].[NH2:24][CH2:25][CH2:26][SH:27].[Na]>ClCCl.C(O)C>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH:15][C:21](=[O:22])[CH2:20][S:27][CH2:26][CH2:25][NH2:24])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 6058CysteamineHCID 6577Chloroacetyl chlorideHCID 5360545SodiumHCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amine

Product 1

HCID 18915889HCID 18915889, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

There was dissolved 15.0 g (0.0604 mol) of 3-[3-(piperidinomethyl)phenoxy]propylamine in 150 ml of dichloromethane and added dropwise 6.82 g (0.0604 mol) of chloroacetyl chloride under cooling with ice. After dropping, the mixture was stirred for 3.5 hours under cooling with ice and then the solvent was removed under reduced pressure. The residue was dissolved in 150 ml of ethanol and this solution was added to a solution which was prepared by adding 4.65 g (0.0604 mol) of 2-aminoethanethiol to a solution of 3.06 g (0.1329 mol) of sodium in 150 ml of ethanol and stirring for 30 minutes at room temperature, and the obtained mixture was refluxed with heating for 3 hours. After being allowed to cool at room temperature, the precipitate was filtrated off, and the solvent was removed under reduced pressure. The obtained residue was dissolved in ethyl acetate and washed with water, and dried over Glauber's salt. Then the solvent was removed under reduced pressure to give 20.4 g of the titled compound as oily matter.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in 150 ml of ethanol
  5. additionthis solution was added to a solution which
  6. customwas prepared
  7. stirringstirring for 30 minutes at room temperature
  8. temperaturethe obtained mixture was refluxed
  9. temperaturewith heating for 3 hours
  10. filtrationthe precipitate was filtrated off
  11. customthe solvent was removed under reduced pressure
  12. dissolutionThe obtained residue was dissolved in ethyl acetate
  13. washwashed with water
  14. dry with materialdried over Glauber's salt
  15. customThen the solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-cf5f3d5226b74647ad4f282963bf2e2d
Source dataset
uspto-grants-1997_09
Patent number
US05672597

Reaction notes

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