Hydrochloric Acid → HCID 70048066, compound

HRID 1648593Notes

Reaction equation

HRID 1648593 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 1.99 N 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-014fb281b3a24ed6b6470580268d4a1c
Source dataset
uspto-grants-1995_07
Patent number
US05436254

Reaction notes

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