Piperidine → HCID 178484018, compound

HRID 967220Notes

Reaction equation

HRID 967220 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]([N:9]([CH2:11][C@H:12]2[CH2:17][CH2:16][C@H:15]([C:18]#[C:19][CH2:20]OS(C)(=O)=O)[CH2:14][CH2:13]2)[CH3:10])=[O:8])=[CH:4][CH:3]=1.[NH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>CO>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7](=[O:8])[N:9]([CH3:10])[CH2:11][C@H:12]2[CH2:17][CH2:16][C@H:15]([C:18]#[C:19][CH2:20][N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[CH2:14][CH2:13]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 178484025HCID 178484025, compound

Product 1

HCID 178484018HCID 178484018, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 222 mg (corresponds to 0.40 mmol) of crude trans-methanesulfonic acid 3-(4-{[(4-chloro-phenoxycarbonyl)-methyl-amino]-methyl}-cyclohexyl)-prop-2-ynyl ester in 4 ml of methanol was cooled to 0° C., treated with 0.34 ml (4 mmol) of piperidine and stirred over night at room temperature. The solvent was evaporated and the residue extracted with aqueous saturated NaHCO3/ether (3×). The organic phase was dried with sodium sulfate, filtered and evaporated. Purification by flash column chromatography on silica gel (methylenechloride/methanol 99:1 to 98:2) gave 92 mg (57%) of pure trans-methyl-[4-(3-piperidin-1-yl-prop-1-ynyl)-cyclohexylmethyl]-carbamic acid 4-chloro-phenyl ester as light yellow viscous oil, MS: 403 (MH+, 1Cl). The following compounds were prepared from the corresponding mesylates and secondary amines:

Workup

  1. customThe solvent was evaporated
  2. extractionthe residue extracted with aqueous saturated NaHCO3/ether (3×)
  3. dry with materialThe organic phase was dried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash column chromatography on silica gel (methylenechloride/methanol 99:1 to 98:2)

Sources & evidence

ORD record
ord-7e6c1f6c1ed24d659637de72c58079a8
Source dataset
uspto-grants-2005_10
Patent number
US06953806B2

Reaction notes

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