N-Methylpropylamine → HCID 178457233, compound

HRID 25642Notes

Reaction equation

HRID 25642 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:22])[N:10]([C@H:12]2[CH2:17][CH2:16][C@H:15](/[CH:18]=[CH:19]/[CH2:20]Cl)[CH2:14][CH2:13]2)[CH3:11])=[CH:4][CH:3]=1.[CH3:23][NH:24][CH2:25][CH2:26][CH3:27]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:22])[N:10]([CH3:11])[C@H:12]2[CH2:17][CH2:16][C@H:15](/[CH:18]=[CH:19]/[CH2:20][N:24]([CH3:23])[CH2:25][CH2:26][CH3:27])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 12315N-MethylpropylamineHCID 178485961HCID 178485961, compound

Product 1

HCID 178457233HCID 178457233, compoundYield 52.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 80 mg (0.23 mmol) of trans-(1E)-[4-(3-Chloro-propenyl)-cyclohexyl]-methyl-carbamic acid 4-chloro-phenyl ester in 4.3 ml of methanol was treated with 0.24 ml (2.34 mmol) N-methylpropylamine and stirred over night at RT. The solvent was evaporated and the residue extracted with aqueous saturated NaHCO3/Et2O (3×). The organic phase was dried with Na2SO4, filtered and evaporated. Purification by flash column chromatography on silica gel (CH2Cl2/MeOH 95:5) gave 46 mg (52%) of trans-(1E)-Methyl-{4-[3-(methyl-propyl-amino)-propenyl]-cyclohexyl}-carbamic acid 4-chloro-phenyl ester, MS: 379 (MH+, 1Cl).

Workup

  1. customThe solvent was evaporated
  2. extractionthe residue extracted with aqueous saturated NaHCO3/Et2O (3×)
  3. dry with materialThe organic phase was dried with Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash column chromatography on silica gel (CH2Cl2/MeOH 95:5)

Sources & evidence

ORD record
ord-030554bc42434fa1b6bb8afc074360d2
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Reaction notes

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