Ammonium Chloride → HCID 22502584, compound

HRID 1251263Notes

Reaction equation

HRID 1251263 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([N:18]3[CH2:23][CH2:22][N:21]([CH2:24][CH3:25])[CH2:20][CH2:19]3)[C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:4][CH:3]=1.[Li]CCCC.[O:31]1[CH2:36][CH2:35][C:34](=[O:37])[CH2:33][CH2:32]1.[Cl-].[NH4+]>O1CCCC1>[CH2:24]([N:21]1[CH2:22][CH2:23][N:18]([C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:17]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([C:34]4([OH:37])[CH2:35][CH2:36][O:31][CH2:32][CH2:33]4)=[CH:7][CH:6]=3)[N:9]=2)[CH2:19][CH2:20]1)[CH3:25]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 121599Tetrahydro-4H-pyran-4-oneHCID 22503615HCID 22503615, compoundHCID 178418339Butyllithium

Product 1

HCID 22502584HCID 22502584, compoundYield 32.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the resulting 3-(4-bromophenyl)-1-(4-ethylpiperazin-1-yl)isoquinoline (0.61 g) in tetrahydrofuran (30 ml) was cooled to −78° C., followed by the dropwise addition of 1.6M n-BuLi (1.1 ml) in nitrogen atmosphere. Fifteen minutes later, a solution of tetrahydropyran-4-one (0.17 g) in tetrahydrofuran (1 ml) was added thereto, and the temperature of the reaction mixture was gradually raised to room temperature. Three hours later, an aqueous solution of saturated ammonium chloride was added thereto, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system), to give the title compound as a pale yellow oil (0.21 g, yield; 32.1%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system)

Sources & evidence

ORD record
ord-aa570c6bc80d42cab9462c1bc634a4bb
Source dataset
uspto-grants-2002_01
Patent number
US06340759B1

Reaction notes

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