Acryloyl chloride → N-[4-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-phenyl]-acrylamide

HRID 643264Notes

Reaction equation

HRID 643264 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:16][C:15]3([CH3:18])[CH2:17][CH:11]2[CH2:12][C:13]([CH3:20])([CH3:19])[CH2:14]3)=[O:9])=[CH:4][CH:3]=1.[C:21](Cl)(=[O:24])[CH:22]=[CH2:23]>C1COCC1>[CH3:18][C:15]12[CH2:17][CH:11]([N:10]([C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:21](=[O:24])[CH:22]=[CH2:23])=[CH:7][CH:6]=3)=[O:9])[CH2:16]1)[CH2:12][C:13]([CH3:20])([CH3:19])[CH2:14]2

Participants

4

Reactant 2

HCID 13140Acryloyl chlorideHCID 577868(4-Amino-phenyl)-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]oct-6-yl)-methanone

Product 1

HCID 68429631N-[4-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-phenyl]-acrylamideYield 47.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4-amino-phenyl)-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]oct-6-yl)-methanone (3.0 g, 11.01 mmol) and TEA (3.1 ml, 22.03 mmol) in dry THF (40 ml) was added dropwise acryloyl chloride (1.07 ml, 13.22 mmol). The mixture was stirred for 45 min., the volatiles evaporated and to the residue added water 25 (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 1.7 g (47%) of N-[4-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-phenyl]-acrylamide as an oil.

Workup

  1. customthe volatiles evaporated and to the residue
  2. additionadded water 25 (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-269571d55965496d9f5336edddf6752f
Source dataset
uspto-grants-2010_04
Patent number
US07700583B2

Reaction notes

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