Chloroacetyl chloride → 2-chloro-N-methyl-N-[4-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-phenyl]-acetamide

HRID 643266Notes

Reaction equation

HRID 643266 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([N:11]2[CH2:17][C:16]3([CH3:19])[CH2:18][CH:12]2[CH2:13][C:14]([CH3:21])([CH3:20])[CH2:15]3)=[O:10])=[CH:5][CH:4]=1.[Cl:22][CH2:23][C:24](Cl)=[O:25]>C1COCC1>[Cl:22][CH2:23][C:24]([N:2]([CH3:1])[C:3]1[CH:4]=[CH:5][C:6]([C:9]([N:11]2[CH2:17][C:16]3([CH3:19])[CH2:18][CH:12]2[CH2:13][C:14]([CH3:21])([CH3:20])[CH2:15]3)=[O:10])=[CH:7][CH:8]=1)=[O:25]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 11414957(4-Methylamino-phenyl)-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]oct-6-yl)-methanone

Product 1

HCID 684324252-chloro-N-methyl-N-[4-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-phenyl]-acetamideYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (4-methylamino-phenyl)-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]oct-6-yl)-methanone (0.6 g, 2.1 mmol) and TEA (0.6 ml, 4.19 mmol) in dry THF (40 ml) was added dropwise chloroacetyl chloride (0.25 ml, 3.14 mmol). The mixture was stirred for 75 min. and evaporated in vacuo followed by addition of water 75 (ml). The aqueous phase was extracted with EtOAc (2×25 ml) and the combined organic phases were dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified on column chromatography (silicagel) using EtOAc-Heptane 1:1 as eluent. Pure fractions were collected; the solvent evaporated in vacuo affording 400 mg (53%) of 2-chloro-N-methyl-N-[4-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-phenyl]-acetamide as a solid.

Workup

  1. customevaporated in vacuo
  2. additionfollowed by addition of water 75 (ml)
  3. extractionThe aqueous phase was extracted with EtOAc (2×25 ml)
  4. dry with materialthe combined organic phases were dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified on column chromatography (silicagel)
  8. customPure fractions were collected
  9. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-eb31caf221b741b58829359d34c05035
Source dataset
uspto-grants-2010_04
Patent number
US07700583B2

Reaction notes

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