Hydrochloric Acid → N-[3-(acetylmethylamino)-2-hydroxypropyl]-N-methylacetamide

HRID 76240Notes

Reaction equation

HRID 76240 reaction equation
[C:1]([CH2:4][NH:5][CH2:6][CH:7]([O:14][Si](C(C)(C)C)(C)C)[CH2:8][N:9]([CH3:13])[C:10](=[O:12])[CH3:11])(=[O:3])[CH3:2].Cl>CO>[C:1]([CH2:4][NH:5][CH2:6][CH:7]([OH:14])[CH2:8][N:9]([CH3:13])[C:10](=[O:12])[CH3:11])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86698891N-[3-(acetylmethylamino)-2-(tert-butyldimethyl silanyloxy)propyl]-N-methylacetamide

Product 1

HCID 86698890N-[3-(acetylmethylamino)-2-hydroxypropyl]-N-methylacetamideYield 95.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-[3-(acetylmethylamino)-2-(tert-butyldimethyl silanyloxy)propyl]-N-methylacetamide (1.12 g, 3.54 mmol) in methanol (23 mL), hydrogen chloride 4M dioxane solution (0.357 mL, 1.426 mmol) was added dropwise at 0° C. and the reaction was stirred at r.t. overnight. Solvent was evaporated and the residue triturated with petroleum ether and decanted. The oil obtained after trituration was dried under vacuum affording N-[3-(acetylmethylamino)-2-hydroxypropyl]-N-methylacetamide (681 mg, 95% yield).

Workup

  1. customSolvent was evaporated
  2. customthe residue triturated with petroleum ether
  3. customdecanted
  4. customThe oil obtained after trituration
  5. customwas dried under vacuum

Sources & evidence

ORD record
ord-1eca467bf16343c4bf56a6b7ef36026a
Source dataset
uspto-grants-2014_09
Patent number
US08835494B2

Reaction notes

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