Hydrochloric Acid → Naratriptan hydrochloride

HRID 358597Notes

Reaction equation

HRID 358597 reaction equation
[CH3:1][NH:2][S:3]([CH2:6][CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[CH:17]1[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]1)(=[O:5])=[O:4].[ClH:24]>C(O)C>[ClH:24].[CH3:1][NH:2][S:3]([CH2:6][CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[CH:17]1[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]1)(=[O:4])=[O:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 4440Naratriptan

Product 1

HCID 60875Naratriptan hydrochlorideYield 79.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the product of Example 1 (50 mg) in hot ethanol (0.5 ml) was added to ethanolic hydrogen chloride [prepared by adding acetyl chloride (33 mg, 0.420 mmol) to ethanol (1 ml) at room temperature] in a stream with stirring at room temperature. A solid crystallised out from the initially clear solution. The suspension was stirred and cooled to 5° over 15 min then filtered under suction. The residue was washed with a little ethanol then dried at 60° in vacuo for 1 h to give the title compound (44 mg) as microcrystals, m.p. 237°-239°.

Workup

  1. customA solid crystallised out from the initially clear solution
  2. stirringThe suspension was stirred
  3. temperaturecooled to 5° over 15 min
  4. filtrationthen filtered under suction
  5. washThe residue was washed with a little ethanol
  6. customthen dried at 60° in vacuo for 1 h

Sources & evidence

ORD record
ord-2efa7c74909a4faf937199a20a4dc610
Source dataset
uspto-grants-1991_03
Patent number
US04997841

Reaction notes

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