Betahistine → HCID 15018133, compound

HRID 973508Notes

Reaction equation

HRID 973508 reaction equation
[CH2:1]([O:8][C:9]([CH:11]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:12][S:13](Cl)(=[O:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:31][NH:32][CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=1>C(Cl)Cl>[CH2:17]([CH:11]([CH2:12][S:13]([N:32]([CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=1)[CH3:31])(=[O:15])=[O:14])[C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 2366BetahistineHCID 8471TriethylamineHCID 15018140HCID 15018140, compound

Product 1

HCID 15018133HCID 15018133, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the resultant compound from Example 62 (1 mmol) in methylene chloride (10 mL) at -10° C. was added triethylamine (1.2 mmol) and 2-(2-methylaminoethyl)pyridine (1 mmol). After 30 min the mixture was evaporated, suspended in ethyl acetate, washed with saturated NaHCO3 solution, water, and brine, and then dried over Na2SO4 and evaporated. Chromatography of the residue on silica gel afforded the desired product.

Workup

  1. customAfter 30 min the mixture was evaporated
  2. washwashed with saturated NaHCO3 solution, water, and brine
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-c54e1b1b3113491182cfcf146647761f
Source dataset
uspto-grants-1991_11
Patent number
US05063208

Reaction notes

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