Hydrochloric Acid → HCID 178501123, compound

HRID 409496Notes

Reaction equation

HRID 409496 reaction equation
Cl.[CH3:2][O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([CH2:12][NH2:13])[CH2:8][CH2:7]1)=[O:5].[C:14](OC(=O)C)(=[O:16])[CH3:15].Cl>N1C=CC=CC=1>[CH3:2][O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([CH2:12][NH:13][C:14](=[O:16])[CH3:15])[CH2:8][CH2:7]1)=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 178501119HCID 178501119, compound

Product 1

HCID 178501123HCID 178501123, compoundYield 103.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of trans-4-(aminomethyl)cyclohexanecarboxylic acid methyl ester hydrochloride (1.5 mmol, 310 mg) in pyridine (2 mL) is added acetic anhydride (1.8 mmol, 0.31 mL) at room temperature. The mixture is stirred at room temperature for 4 hours, poured into 1M HCl and ice-water, and then extracted with ethyl acetate. The combined organic phase is washed with water and brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain trans-4-(acetamidomethyl)-1-cyclohexanecarboxylic acid methyl ester (330 mg) as colorless oil. ESI-MS m/z: 214 [M+1]+, Retention time 1.97 min (condition B).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic phase is washed with water and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1f569d5f51264f0b90e4a1cdc765f5a8
Source dataset
uspto-grants-2014_06
Patent number
US08759365B2

Reaction notes

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