4-Methylpiperidine → HCID 57845317, compound

HRID 734901Notes

Reaction equation

HRID 734901 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.CS(O[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]#[C:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)=[CH:25][N:24]=2)=[CH:17][C:16]=1[CH3:36])(=O)=O>CN(C=O)C>[Cl:35][C:32]1[CH:31]=[CH:30][C:29]([C:26]2[CH:27]=[CH:28][C:23]([C:22]#[C:21][C:18]3[CH:19]=[CH:20][C:15]([CH2:14][CH2:13][N:5]4[CH2:6][CH2:7][CH:2]([CH3:1])[CH2:3][CH2:4]4)=[C:16]([CH3:36])[CH:17]=3)=[N:24][CH:25]=2)=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 693814-MethylpiperidineHCID 86601141HCID 86601141, compound

Product 1

HCID 57845317HCID 57845317, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
69 °C

Procedure

0.09 mL (0.77 mmol) of 4-methylpiperidine was added to a solution of 110 mg (0.26 mmol) of 2-{4-[5-(4-chlorophenyl)pyridin-2-ylethynyl]-2-methylphenyl}ethyl methanesulfonate in 2 mL of DMF and heated to 69° C. After the reaction had ended, the reaction solution was cooled and the precipitate formed was suction filtered. Yield: 40 mg (36% of theoretical); C28H29ClN2 (M=428.996) C28H29ClN2; calc.: molpeak (M+H)+:429/431 (Cl); found: molpeak (M+H)+:429/431 (Cl); HPLC-MS: 5.96 minutes (method G).

Workup

  1. temperaturethe reaction solution was cooled
  2. customthe precipitate formed
  3. filtrationfiltered
  4. custom5.96 minutes (method G)

Sources & evidence

ORD record
ord-f761cda7c43e4900a01793c0395fed71
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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