HCID 18621499, compound → HCID 18621544, compound

HRID 324557Notes

Reaction equation

HRID 324557 reaction equation
C([O:9][CH2:10][C:11]#[C:12][CH2:13][N:14]1[CH2:19][CH2:18][CH:17]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16][CH2:15]1)(=O)C1C=CC=CC=1>CO>[CH2:20]([CH:17]1[CH2:16][CH2:15][N:14]([CH2:13][C:12]#[C:11][CH2:10][OH:9])[CH2:19][CH2:18]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

3

Reactant 1

HCID 18621499HCID 18621499, compound

Product 1

HCID 18621544HCID 18621544, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A steam of ammonia gas was bubbled through dry-ice/acetone cooled methanol until the concentration of ammonia was about 20%. To this solution was added a solution of 1-(4-benzoyloxybut-2-yn-1-yl)-4-benzylpiperidine (300 mg, 0.860 mmol) in 2 mL of methanol. The resulting solution was allowed to stir at room temperature for 24 hr. Methanol was evaporated in vacuo to give a residue, which was purified by flash chromatography to give the title compound as a brown oil (140 mg, 67%): 1H NMR (CDCl3) d 1.35 (m, 2 H), 1.50 (m, 1 H), 1.62 (m, 2 H), 2.08 (m, 2 H), 2.51 (d, J=6.9 Hz, 2 H), 2.89 (d, J=11.1 Hz, 2 H), 3.25 (s, 2 H), 4.24 (s, 2 H), 4.50 (bs, 1 H), 7.10-7.26 (m, 5 H). HRMS calcd for C16H21NO 243.1613, found 243.1618.

Workup

  1. customA steam of ammonia gas was bubbled through dry-ice/acetone
  2. temperaturecooled methanol until the concentration of ammonia
  3. customMethanol was evaporated in vacuo
  4. customto give a residue, which
  5. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-4d43d9a2cbb249329e698cdb7aca4a4d
Source dataset
uspto-grants-2001_04
Patent number
US06218404B1

Reaction notes

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