Sodium amide → 1-{1-[4-(1-Butenyl)benzoyl]-4-piperidinyl}-3,4-dihydrocarbostyril

HRID 1708295Notes

Reaction equation

HRID 1708295 reaction equation
[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:3][CH3:4].[CH3:24][C:25]([CH3:28])([O-])[CH3:26].[K+].[NH2-].[Na+].C(C1C=[CH:57][C:37]([C:38]([N:40]2[CH2:45][CH2:44][CH:43]([N:46]3[C:56]4[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=4)[CH2:50][CH2:49][C:47]3=[O:48])[CH2:42][CH2:41]2)=[O:39])=[CH:36]C=1)=O>O.O1CCCC1>[CH:24]([C:25]1[CH:28]=[CH:57][C:37]([C:38]([N:40]2[CH2:45][CH2:44][CH:43]([N:46]3[C:56]4[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=4)[CH2:50][CH2:49][C:47]3=[O:48])[CH2:42][CH2:41]2)=[O:39])=[CH:36][CH:26]=1)=[CH:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 24533Sodium amideHCID 80374Propyltriphenylphosphonium bromideHCID 19030828HCID 19030828, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 538484951-{1-[4-(1-Butenyl)benzoyl]-4-piperidinyl}-3,4-dihydrocarbostyrilYield 931.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of propyltriphenylphosphonium bromide (2.34 g), potassium-t-butoxide (62 mg) and sodium amide powder (0.3 g) is added tetrahydrofuran (110 ml) under argon atmosphere and the mixture is stirred at room temperature for 3 hours. To the resulting yellowish red solution is added 1-[1-(4-formylbenzoyl)-4-piperidinyl]-3,4-dihydrocarbostyril (2 g) gradually under ice cooling and the mixture is stirred under the same conditions for 3 hours. The reaction mixture is poured into water and extracted with ethyl acetate/toluene and then dried over sodium carbonate. The resultant is purified by silica gel column chromatography (solvent: n-hexane:ethyl acetate=1:1) to give 1-{1-[4-(1-butenyl)benzoyl]-4-piperidinyl}-3,4-dihydrocarbostyril (2 g).

Workup

  1. stirringthe mixture is stirred under the same conditions for 3 hours
  2. extractionextracted with ethyl acetate/toluene
  3. dry with materialdried over sodium carbonate
  4. customThe resultant is purified by silica gel column chromatography (solvent: n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-eed03cb5f06c4109a6ced2a943ff7aeb
Source dataset
uspto-grants-1994_10
Patent number
US05356904

Reaction notes

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