Pyridine → HCID 19992016, compound

HRID 345294Notes

Reaction equation

HRID 345294 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH2:5]([C:8]12[CH2:15][O:14][C:11]([CH:16]3[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]3)([O:12][CH2:13]1)[O:10][CH2:9]2)[CH2:6][CH3:7].N1C=CC=CC=1>ClCCl>[C:1]([N:18]1[CH2:19][CH2:20][CH2:21][CH:16]([C:11]23[O:10][CH2:9][C:8]([CH2:5][CH2:6][CH3:7])([CH2:13][O:12]2)[CH2:15][O:14]3)[CH2:17]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 19991999HCID 19991999, compound

Product 1

HCID 19992016HCID 19992016, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (81 μl) was added to a stirred solution of 3-(4-n-propyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)piperidine (0.25 g.) and pyridine (92 μl) in dichloromethane (15 ml) at 0°. The mixture was stirred at room temperature for 3 hours. The mixture was washed with water, saturated aqueous sodium hydrogen carbonate solution and finally brine. The dichloromethane extracts were dried over anhydrous magnesium sulphate and evaporated in vacuo. The residue was purified by chromatography on alumina (Alumina Woelm TSC) eluting with 1:3 dichlormethane:hexane, saturated with ammonia. N-Acetyl- 3-(4-n-propyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)piperidine (0.15 g.) was obtained as a colourless oil.

Workup

  1. washThe mixture was washed with water, saturated aqueous sodium hydrogen carbonate solution and finally brine
  2. dry with materialThe dichloromethane extracts were dried over anhydrous magnesium sulphate
  3. customevaporated in vacuo
  4. customThe residue was purified by chromatography on alumina (Alumina Woelm TSC)
  5. washeluting with 1:3 dichlormethane

Sources & evidence

ORD record
ord-a0690705058d4aaba52604b75f478a70
Source dataset
uspto-grants-1991_10
Patent number
US05057504

Reaction notes

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