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Benzyl Alcohol → 4-(1-Benzyloxy-7-chloro-isoquinolin-6-yloxy)-piperidine-1-carboxylic acid tert-butyl-ester

HRID 1255418
Notes
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Reaction equation

HRID 1255418 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[C:18]1[C:27]2[C:22](=[CH:23][C:24](F)=[C:25]([Cl:28])[CH:26]=2)[CH:21]=[CH:20][N:19]=1.[CH2:30]([OH:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CC(N(C)C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:24]2[CH:23]=[C:22]3[C:27](=[CH:26][C:25]=2[Cl:28])[C:18]([O:37][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[N:19][CH:20]=[CH:21]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 244Benzyl Alcohol2×HCID 24758Sodium hydride3×HCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 598182461,7-Dichloro-6-fluoroisoquinoline

Product 1

HCID 576525114-(1-Benzyloxy-7-chloro-isoquinolin-6-yloxy)-piperidine-1-carboxylic acid tert-butyl-ester

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

289.8 mg (1.44 mmol) of 4-hydroxy-piperidine-1-carboxylic acid tert-butyl-ester were dissolved in 10 ml of dimethyl acetamide and 57.6 mg (1.44 mmol) of sodium hydride (60%) were added. The reaction mixture was stirred at room temperature. After 30 minutes a solution of 310 mg (1.44 mmol) of 1,7-dichloro-6-fluoro-isoquinoline (5) in 3 ml of dimethyl acetamide was added and the mixture was stirred at room temperature for 1 h to complete conversion. Then 155.7 mg (1.44 mmol) of benzyl alcohol followed by 57.6 mg (1.44 mmol) of sodium hydride (60%) were added and stirring was continued at room temperature. To reach complete conversion, 0.5 equivalents of benzyl alcohol and sodium hydride were added twice, after 2 h and standing overnight. For working up, the solvent was evaporated, the residue was taken up in dichloromethane, washed twice with H2O, dried with MgSO4 and evaporated. Final purification was accomplished by preparative HPLC.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 h
  2. additionwere added
  3. stirringstirring
  4. customwas continued at room temperature
  5. additionwere added twice, after 2 h
  6. customthe solvent was evaporated
  7. washwashed twice with H2O
  8. dry with materialdried with MgSO4
  9. customevaporated
  10. customFinal purification

Sources & evidence

ORD record
ord-5a6626cb3db447838d372d1e58688018
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08461144B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes