Chlorosuccinimide → 2-[(3-Chloro-2-hydroxymethyl-pyridin-4-yl)-methylamino]-ethanol

HRID 1637627Notes

Reaction equation

HRID 1637627 reaction equation
[Cl:1]N1C(=O)CCC1=O.[OH:9][CH2:10][C:11]1[CH:16]=[C:15]([N:17]([CH3:21])[CH2:18][CH2:19][OH:20])[CH:14]=[CH:13][N:12]=1>C(O)(=O)C>[Cl:1][C:16]1[C:11]([CH2:10][OH:9])=[N:12][CH:13]=[CH:14][C:15]=1[N:17]([CH3:21])[CH2:18][CH2:19][OH:20]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 187993842-[(2-Hydroxymethyl-pyridin-4-yl)-methyl-amino]-ethanol

Product 1

HCID 537528042-[(3-Chloro-2-hydroxymethyl-pyridin-4-yl)-methylamino]-ethanol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

N-Chlorosuccinimide (25 g, 187 mmol) is added in 5 portions to a solution of 2-[(2-hydroxymethyl-pyridin-4-yl)-methyl-amino]-ethanol (30 g of the crude product isolated in step a), 140 mmol) in acetic acid (170 ml) over a period of 3 h. Stirring is continued for I h and the solvent is evaporated in vacuo. The residue is treated with 6N sodium hydroxide solution and extracted with ethyl acetate. The combined organic extracts are washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue is chromatographed (silica, toluene/dioxane 2:1) to give the title compound as a brown solid. M.p. 49-53° C.

Workup

  1. customthe solvent is evaporated in vacuo
  2. additionThe residue is treated with 6N sodium hydroxide solution
  3. extractionextracted with ethyl acetate
  4. washThe combined organic extracts are washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue is chromatographed (silica, toluene/dioxane 2:1)

Sources & evidence

ORD record
ord-0f5d6ba912894d34b2a78b56778cc574
Source dataset
uspto-grants-2000_03
Patent number
US06043242

Reaction notes

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