Water → HCID 178501123, compound

HRID 131284Notes

Reaction equation

HRID 131284 reaction equation
Cl.[NH2:2][CH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]([O:12][CH3:13])=[O:11])[CH2:6][CH2:5]1.C(N(CC)CC)C.[C:21](Cl)(=[O:23])[CH3:22].O>C(Cl)(Cl)Cl>[C:21]([NH:2][CH2:3][C@H:4]1[CH2:5][CH2:6][C@H:7]([C:10]([O:12][CH3:13])=[O:11])[CH2:8][CH2:9]1)(=[O:23])[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 178501119HCID 178501119, compound

Product 1

HCID 178501123HCID 178501123, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of methyl trans-4-(aminomethyl)cyclohexanecarboxylate hydrochloride (5.86 g) and triethylamine (12 mL) in chloroform (100 mL) is added dropwise acetyl chloride (2.69 g) under ice-cooling and the mixture is stirred at room temperature for 2 hours. The reaction mixture is poured into water and the mixture is extracted with chloroform (×2). The combined extracts are washed successively with 10% HCl, saturated brine, a saturated sodium hydrogencarbonate solution, and saturated brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue is purified by flash column chromatography on silica gel (Solvent; n-hexane:ethyl acetate=1:1→0:1) to give methyl trans-4-(acetylaminomethyl)cyclohexanecarboxylate (5.92 g, yield; 98%) as an amorphous powder. MS (APCI) m/z; 214 [M+H]+

Workup

  1. temperaturecooling
  2. extractionthe mixture is extracted with chloroform (×2)
  3. washThe combined extracts are washed successively with 10% HCl, saturated brine
  4. dry with materiala saturated sodium hydrogencarbonate solution, and saturated brine, dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by flash column chromatography on silica gel (Solvent; n-hexane:ethyl acetate=1:1→0:1)

Sources & evidence

ORD record
ord-d4d5036856b74f7f97f60f8e41c483de
Source dataset
uspto-grants-2008_06
Patent number
US07384952B2

Reaction notes

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