Hydrochloric Acid → HCID 70048066, compound

HRID 266831Notes

Reaction equation

HRID 266831 reaction equation
C([N-]C(C)C)(C)C.[Li+].[CH:9]([C:11]1[CH:35]=[CH:34][C:14]([C:15]([N:17]2[CH2:22][CH2:21][CH:20]([N:23]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH2:27][CH2:26][C:24]3=[O:25])[CH2:19][CH2:18]2)=[O:16])=[CH:13][CH:12]=1)=O.Cl.[O:37]1C[CH2:40][CH2:39][CH2:38]1>>[OH:37][CH2:38][CH2:39][CH:40]=[CH:9][C:11]1[CH:35]=[CH:34][C:14]([C:15]([N:17]2[CH2:18][CH2:19][CH:20]([N:23]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH2:27][CH2:26][C:24]3=[O:25])[CH2:21][CH2:22]2)=[O:16])=[CH:13][CH:12]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 2724682Lithium diisopropylamideHCID 190308281-[1-(4-Formylbenzoyl)-4-piperidinyl]-3,4-dihydrocarbostyril

Product 1

HCID 70048066HCID 70048066, compound

Procedure

4-Hydroxypropyltriphenylphosphonium bromide (2.4 g) is dispersed into tetrahydrofuran (50 ml) and thereto is added dropwise lithium diisopropylamide (a solution in 1.99N tetrahydrofuran) (6.1 ml) at 0°-5° C. After adding, the mixture is stirred at 0°-5° C. for 1 hour and thereto is added 1-[1-(4-formylbenzoyl)-4-piperidinyl]-3,4-dihydrocarbostyril (2 g). The mixture is stirred at room temperature overnight. The reaction mixture is poured into ice-water and adjusted to pH 4-5 by adding conc. hydrochloric acid. The mixture is extracted with ethyl acetate and dried with magnesium sulfate. The solvent is distilled off and the resulting residue is purified by silica gel column chromatography (solvent: n-hexane:ethyl acetate=1:1→ethyl acetate:methanol=20:1) to give 1-{1-[4-(4-hydroxy-1-butenyl)benzoyl]-4-piperidinyl}-3,4-dihydrocarbostyril (1 g).

Workup

  1. additionAfter adding
  2. stirringThe mixture is stirred at room temperature overnight
  3. extractionThe mixture is extracted with ethyl acetate
  4. dry with materialdried with magnesium sulfate
  5. distillationThe solvent is distilled off
  6. customthe resulting residue is purified by silica gel column chromatography (solvent: n-hexane:ethyl acetate=1:1→ethyl acetate:methanol=20:1)

Sources & evidence

ORD record
ord-d3816f7a1790441691806e24bce93e86
Source dataset
uspto-grants-1997_07
Patent number
US05652247

Reaction notes

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