Acetic Anhydride → HCID 19004213, compound

HRID 2225435Notes

Reaction equation

HRID 2225435 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C:9]1[CH:37]=[CH:36][C:12]([CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([CH2:21][O:22][CH:23]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:17][CH2:16]2)=[CH:11][CH:10]=1.C(N(CC)CC)C>C(#N)C>[C:1]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][CH2:14][N:15]2[CH2:16][CH2:17][CH:18]([CH2:21][O:22][CH:23]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:19][CH2:20]2)=[CH:36][CH:37]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 19004206HCID 19004206, compound

Product 1

HCID 19004213HCID 19004213, compoundYield 17.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Acetic anhydride (68 mg, 0.67 mmol) was added dropwise to a stirred solution of 1-(4-aminophenethyl)-4-(diphenylmethoxymethyl)piperidine (180 mg, 0.45 mmol) (see Example 21) and triethylamine (55 mg, 0.54 mmol) in acetonitrile (5 ml) and the mixture heated under reflux for 2 hours and evaporated. The residue was partitioned between ethyl acetate and 10% aqueous potassium carbonate and the layers separated. The aqueous layer was extracted into ethyl acetate and the combined organic layers were dried over magnesium sulphate and evaporated. The residue was triturated with ethyl acetate and the resulting solid collected, washed with ethyl acetate and dried to give the title compound (35 mg) as an off-white solid which was characterised containing 0.25 equivalents of water.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 2 hours
  3. customevaporated
  4. customThe residue was partitioned between ethyl acetate and 10% aqueous potassium carbonate
  5. customthe layers separated
  6. extractionThe aqueous layer was extracted into ethyl acetate
  7. dry with materialthe combined organic layers were dried over magnesium sulphate
  8. customevaporated
  9. customThe residue was triturated with ethyl acetate
  10. customthe resulting solid collected
  11. washwashed with ethyl acetate
  12. customdried

Sources & evidence

ORD record
ord-7aad165c87694e6a8c3c0356bcbb2874
Source dataset
uspto-grants-1994_09
Patent number
US05344835

Reaction notes

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