Sodium Iodide → HCID 178457230, compound

HRID 967228Notes

Reaction equation

HRID 967228 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:23])[N:10]([CH2:12][C@H:13]2[CH2:18][CH2:17][C@H:16]([C:19]#[C:20][CH2:21]Cl)[CH2:15][CH2:14]2)[CH3:11])=[CH:4][CH:3]=1.[Na+].[I-].[CH3:26][NH:27][CH2:28][CH2:29][CH3:30]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:23])[N:10]([CH3:11])[CH2:12][C@H:13]2[CH2:18][CH2:17][C@H:16]([C:19]#[C:20][CH2:21][N:27]([CH3:26])[CH2:28][CH2:29][CH3:30])[CH2:15][CH2:14]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 12315N-MethylpropylamineHCID 178484012HCID 178484012, compound

Product 1

HCID 178457230HCID 178457230, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 250 mg (0.63 mmol) of trans-[4-(3-chloro-prop-1-ynyl)cyclohexyl-methyl]-methyl-carbamic acid 4-fluoro-phenyl ester with a catalytic amount of NaI in 7 ml of methanol was treated with 0.65 ml (6.3 mmol) of N-methylpropylamine 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 98:2) gave 218 mg (93%) of pure trans-methyl-{4-[3-(methyl-propyl-amino)-prop-1-ynyl]-cyclohexylmethyl}-carbamic acid 4-fluoro-phenyl ester as light brown oil, MS: 375 (MH+).

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 98:2)

Sources & evidence

ORD record
ord-4938d9473bf84b56b79f08855bf872a5
Source dataset
uspto-grants-2005_10
Patent number
US06953806B2

Reaction notes

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