Triethylamine → HCID 54042425, compound

HRID 613256Notes

Reaction equation

HRID 613256 reaction equation
O=[C:2]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][CH:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)=[CH:10][CH:9]=1)[CH2:3][CH2:4][C:5]([OH:7])=[O:6].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:38]([O:45][NH2:46])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(N(CC)CC)C>C1COCC1>[CH2:38]([O:45][N:46]=[C:2]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][CH:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)=[CH:10][CH:9]=1)[CH2:3][CH2:4][C:5]([OH:7])=[O:6])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 102313O-BenzylhydroxylamineHCID 15463122HCID 15463122, compound

Product 1

HCID 54042425HCID 54042425, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Oxo-4-[4-(4-phenyl-piperidin-1-yl)-phenyl]-butyric acid (1.0 g, 2.96 mmol) (Example 1) and carbonyldimidazole (0.51 g, 3.11 mmol) were stirred for 18 hours at room temperature under nitrogen. A slurry of O-Benzylhydroxylamine (0.57 g, 3.55 mmol) and triethylamine (0.49 mL, 3.55 mol) in THF (5 mL) was added in one portion and the resulting mixture refluxed for 18 hours, filtered, and washed with THF (50 mL). The filtrate was concentrated and columned on silica gel eluting with 50% ethyl acetate in hexanes to give 4-benzyloxyimino-4-[4-(4-phenyl-piperidin-1-yl)-phenyl]-butyric acid (0.68 g, %C,H,N found: 76.01, 6.89, 6.26).

Workup

  1. temperaturethe resulting mixture refluxed for 18 hours
  2. filtrationfiltered
  3. washwashed with THF (50 mL)
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-e84646f44abf4e848f2364e55f30899f
Source dataset
uspto-grants-1999_12
Patent number
US06008220

Reaction notes

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