Tetrahydrofuran → 1-Benzyl-4-(2-chloro-6-methoxyquinolin-3-yl)piperidin-4-ol

HRID 469322Notes

Reaction equation

HRID 469322 reaction equation
C([N-]C(C)C)(C)C.[Li+].[Cl:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:20][CH3:21])[CH:16]=2)[N:11]=1.[CH2:22]([N:29]1[CH2:34][CH2:33][CH2:32][CH2:31][C:30]1=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1C[O:39]CC1>>[CH2:22]([N:29]1[CH2:34][CH2:33][C:32]([C:19]2[C:10]([Cl:9])=[N:11][C:12]3[C:17]([CH:18]=2)=[CH:16][C:15]([O:20][CH3:21])=[CH:14][CH:13]=3)([OH:39])[CH2:31][CH2:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 836472-Chloro-6-methoxyquinolineHCID 2724682Lithium diisopropylamideHCID 51700761-Benzyl-2-piperidone

Product 1

HCID 581811261-Benzyl-4-(2-chloro-6-methoxyquinolin-3-yl)piperidin-4-ol

Conditions

Temperature
-78 °C

Procedure

Under an argon atmosphere 14.0 mL (28.0 mmol) of a 2 M lithium diisopropylamide solution in 50 mL THF were cooled to −78° C. and combined with stirring with a solution of 5.00 g (25.1 mmol) of 2-chloro-6-methoxy-quinoline in THF. After 1 h stirring at −78° C., 4.5 mL (25.2 mmol) N-benzylpiperidone were added dropwise. After 1 h stirring at −78° C. the mixture was allowed to come up to RT and stirred overnight. The mixture was evaporated down i. vac. and purified by flash chromatography through Alox. The fractions containing the product were combined and evaporated down.

Workup

  1. stirringAfter 1 h stirring at −78° C. the mixture
  2. customto come up to RT
  3. stirringstirred overnight
  4. customThe mixture was evaporated down i
  5. customand purified by flash chromatography through Alox
  6. additionThe fractions containing the product
  7. customevaporated down

Sources & evidence

ORD record
ord-86951bac4dce423987c5afaee4886243
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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