Methanol → HCID 69784770, compound

HRID 1063373Notes

Reaction equation

HRID 1063373 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([N:11]2[CH2:16][CH2:15][CH:14]([C:17]#[C:18][CH2:19]OS(C)(=O)=O)[CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1.C[CH:26]=[CH:27][CH2:28][NH2:29].[OH-].[Na+].[CH3:32]O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([N:11]2[CH2:16][CH2:15][CH:14]([C:17]#[C:18][CH2:19][N:29]([CH2:28][CH:27]=[CH2:26])[CH3:32])[CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 304472-Buten-1-amineHCID 86585280HCID 86585280, compound

Product 1

HCID 69784770HCID 69784770, compoundYield 70%

Procedure

A solution of 320 mg (0.83 mmol) of 4-(3-Methanesulfonyloxy-prop-1-ynyl)-piperidine-1-carboxylic acid 4-chloro-phenyl ester and 0.79 ml (8.3mmol) of N-methylallylamine in 7 ml of methanol was stirred over night at RT. Then an aqueous solution of 1N NaOH was added and extracted with ether (3×). The organic phase was dried with Na2SO4, filtered and evaporated. The residue was purified by flash column chromatography on silica gel (CH2Cl2/MeOH 19:1 to 9:1) to yield 201 mg (70%) of pure 4-[3-(Allyl-methyl-amino)-prop 1 ynyl]-piperidine-1-carboxylic acid 4-chloro-phenyl ester, MS: 347 (MH+, 1Cl).

Workup

  1. extractionextracted with ether (3×)
  2. dry with materialThe organic phase was dried with Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by flash column chromatography on silica gel (CH2Cl2/MeOH 19:1 to 9:1)

Sources & evidence

ORD record
ord-d2d41bc8f15e4cf7ba8a7a27c3080b50
Source dataset
uspto-grants-2005_11
Patent number
US06964974B2

Reaction notes

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