Water → HCID 59226240, compound

HRID 1621299Notes

Reaction equation

HRID 1621299 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:23]([O:30][C:31]1[C:40]2[C:35](=[CH:36][C:37](F)=[C:38]([Cl:41])[CH:39]=2)[CH:34]=[CH:33][N:32]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O>CC(N(C)C)=O>[CH2:23]([O:30][C:31]1[C:40]2[C:35](=[CH:36][C:37]([O:14][C:11]3([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH2:10][CH2:9][N:8]([CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH2:13][CH2:12]3)=[C:38]([Cl:41])[CH:39]=2)[CH:34]=[CH:33][N:32]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydride2×HCID 973334-Piperidinol, 1-benzyl-4-phenyl-HCID 598182521-Benzyloxy-7-chloro-6-fluoro-isoquinoline

Product 1

HCID 59226240HCID 59226240, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

566 mg of 1-Benzyl-4-phenyl-piperidin-4-ol (67) were dissolved in 6 ml of dry dimethyl acetamide. 48 mg of sodium hydride (95%) were added and after 1 h of stirring, 580 mg of 1-benzyloxy-7-chloro-6-fluoro-isoquinoline (61), dissolved in 6 ml of dry dimethyl acetamide were added. The course of the reaction was monitored by LCMS and 50 mg of sodium hydride were added several times until no further conversion could be observed. 10 mL of water were added. The resulting precipitate was purified by silica gel chromatography to give 930 mg of the desired product, sufficiently pure for further conversion. Rt=1.62 min (Method C). Detected mass: 536.2 (M+H+).

Workup

  1. additionwere added
  2. additionwere added several times until no further conversion
  3. customThe resulting precipitate was purified by silica gel chromatography

Sources & evidence

ORD record
ord-ad6c03c0a62543429a44b5d7e74e53ca
Source dataset
uspto-grants-2014_07
Patent number
US08772492B2

Reaction notes

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