Diketene → HCID 10691927, compound

HRID 382669Notes

Reaction equation

HRID 382669 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[CH3:7][NH:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][C:15]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:14][CH2:13]1>C1(C)C=CC=CC=1>[C:18]1([C:15]2([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:14][CH2:13][N:12]([CH2:11][CH2:10][CH2:9][N:8]([CH3:7])[C:4](=[O:5])[CH2:3][C:2]([CH3:1])=[O:6])[CH2:17][CH2:16]2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 12661DiketeneHCID 23004130HCID 23004130, compound

Product 1

HCID 10691927HCID 10691927, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Diketene (0.98 mL, 12.7 mmol, 1.50 equiv) was added at 0° C. to a stirred solution of 1-[3-(N-methylamino)propyl]-4,4-diphenylpiperidine (2.61 g, 8.46 mmol, 1.00 equiv) in anhydrous toluene (30 mL) under argon, and stirring was continued for 1 hour. After removal of the solvent, the residue was purified by flash chromatography (SiO2, EtOAc-MeOH-isopropylamine 9:1:0 to 6:1:0.1) to afford 2.97 g (89%) of brown oil, which was characterized spectroscopically.

Workup

  1. customAfter removal of the solvent
  2. customthe residue was purified by flash chromatography (SiO2, EtOAc-MeOH-isopropylamine 9:1:0 to 6:1:0.1)

Sources & evidence

ORD record
ord-e028f2dc403546a8aacf0a0d585a52e2
Source dataset
uspto-grants-2001_10
Patent number
US06310076B1

Reaction notes

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