Dimethylamine → HCID 178483440, compound

HRID 25646Notes

Reaction equation

HRID 25646 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]([N:9]([CH3:25])[C@H:10]2[CH2:15][CH2:14][C@H:13]([C:16]#[C:17][CH2:18][CH2:19]OS(C)(=O)=O)[CH2:12][CH2:11]2)=[O:8])=[CH:4][CH:3]=1.[CH3:28][NH:29][CH3:30]>CO>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7](=[O:8])[N:9]([C@H:10]2[CH2:15][CH2:14][C@H:13]([C:16]#[C:17][CH2:18][CH2:19][N:29]([CH3:30])[CH3:28])[CH2:12][CH2:11]2)[CH3:25])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 178485962HCID 178485962, compound

Product 1

HCID 178483440HCID 178483440, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 400 mg (corresponds to 0.69 mmol) of crude trans-Methanesulfonic acid 4-{4-[(4-chloro-phenoxycarbonyl)-methyl-amino]-cyclohexyl}-but-3-ynyl ester in 4 ml of methanol was treated with 1.23 ml (6.88 mmol) Dimethylamine (33% in EtOH, 5.6M) and stirred over night at RT. The reaction was heated at 70° C. for 2 h, cooled, 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 99:1 to 9:1) gave 84 mg (34%) of trans-[4-(4-Dimethylamino-but-1-ynyl)-cyclohexyl]-methyl-carbamic acid 4-chloro-phenyl ester, MS: 363 (MH+, 1Cl).

Workup

  1. temperatureThe reaction was heated at 70° C. for 2 h
  2. temperaturecooled
  3. customevaporated
  4. extractionthe residue extracted with aqueous saturated NaHCO3/Et2O (3×)
  5. dry with materialThe organic phase was dried with Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customPurification by flash column chromatography on silica gel (CH2Cl2/MeOH 99:1 to 9:1)

Sources & evidence

ORD record
ord-0ded742a8518442d9c99a8e3f4d553ff
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Reaction notes

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