1-Methylisoquinoline → HCID 9974538, compound

HRID 2268174Notes

Reaction equation

HRID 2268174 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[Li+].CC([N-]C(C)C)C.I[CH2:21][CH:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]1>C1COCC1>[C:2]1([CH2:1][CH2:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])[CH2:24][CH2:23]2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 155921-MethylisoquinolineHCID 2724682Lithium diisopropylamideHCID 10448961Tert-butyl 4-(iodomethyl)piperidine-1-carboxylate

Product 1

HCID 9974538HCID 9974538, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

The procedure described in Example 7a was followed using 1-methyl isoquinoline (0.50 g, 3.49 mmol), 1M LDA (4.2 mL, 4.2 mmol), and 4-iodomethyl-1-piperidinecarboxylic acid, 1-(1,1-dimethylethyl) ester (1.2 g, 3.84 mmol) in dry THF (45 mL) except that after addition of the reagents, the mixture was stirred at −78° C. for 1.75 hours. Purification by chromatography (30% EtOAc/toluene) gave the title compound (0.784 g, 66%) as a yellow oil.

Workup

  1. additionafter addition of the reagents
  2. customPurification by chromatography (30% EtOAc/toluene)

Sources & evidence

ORD record
ord-a837d21c20ea4bb3b789ad06f355cd78
Source dataset
uspto-grants-2001_12
Patent number
US06326382B1

Reaction notes

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