Hydrochloric Acid → 6-[(6-Methylpyridin-2-yl)methyl]-1,4-oxazepane dihydrochloride

HRID 1808240Notes

Reaction equation

HRID 1808240 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][CH:9]2[CH2:15][O:14][CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]2)[CH:5]=[CH:4][CH:3]=1.[ClH:23]>C(O)(C)C>[ClH:23].[ClH:23].[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][CH:9]2[CH2:15][O:14][CH2:13][CH2:12][NH:11][CH2:10]2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86630785tert-Butyl 6-[(6-methylpyridin-2-yl)methyl]-1,4-oxazepane-4-carboxylate

Product 1

HCID 685362146-[(6-Methylpyridin-2-yl)methyl]-1,4-oxazepane dihydrochlorideYield 85.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

tert-Butyl 6-[(6-methylpyridin-2-yl)methyl]-1,4-oxazepane-4-carboxylate (Preparation 83, 42.5 g, 0.14 mol, 1 eq) was dissolved in isopropanol (250 mL), concentrated hydrogen chloride (38 mL, 0.42 mol, 3 eq) was added under stirring, and the mixture was refluxed for 2 h. The reaction mixture was then evaporated, and the residue was coevaporated twice with isopropanol. The product was crystallized from isopropanol, and the crystals were washed with diethylether/isopropanol (3:1) mixture and ether and finally vacuum-dried to give title compound as white crystals (32.3 g, 0.12 mol, 82%).

Workup

  1. temperaturethe mixture was refluxed for 2 h
  2. customThe reaction mixture was then evaporated
  3. customThe product was crystallized from isopropanol
  4. washthe crystals were washed with diethylether/isopropanol (3:1) mixture and ether
  5. customfinally vacuum-dried

Sources & evidence

ORD record
ord-b3d94292e0cb4e768ea1075ceccd9a70
Source dataset
uspto-grants-2013_01
Patent number
US08357711B2

Reaction notes

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