Acetic Anhydride → 2-Phenylazepane-1-carbaldehyde

HRID 1683186Notes

Reaction equation

HRID 1683186 reaction equation
C(O[C:5](=[O:7])C)(=O)C.[C:8]1([CH:14]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][NH:15]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(O)=O>[CH:5]([N:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:14]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:7]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 44288382-phenylazepane

Product 1

HCID 124781742-Phenylazepane-1-carbaldehydeYield 97%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of, 98-100% formic acid (30 ml) and acetic anhydride (100 ml) was added 2-(R,S)-phenylazacycloheptane (10 g, 57.1 mmol; B. E. Maryanoff et al., J.Med. Chem., 30, 1433, 1987) and the mixture warmed to 70° C. for 2 h. The reaction mixture was then cooled and evaporated to dryness in vacuo and the residue was partitioned between ether and saturated aqueous potassium carbonate. The ether layer was separated and evaporated to dryness in vacuo to afford the title compound (11.24 g; 97%) as a mixture of E/Z isomers.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. customevaporated to dryness in vacuo
  3. customthe residue was partitioned between ether and saturated aqueous potassium carbonate
  4. customThe ether layer was separated
  5. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-7bfdd27bc76d4215957779909bb598da
Source dataset
uspto-grants-1997_06
Patent number
US05637600

Reaction notes

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