Hydrochloric Acid → HCID 178484819, compound

HRID 409495Notes

Reaction equation

HRID 409495 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([N:11](C(OC(C)(C)C)=O)[CH3:12])[CH2:7][CH2:6]1)=[O:4].[ClH:20]>CCOC(C)=O>[ClH:20].[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][CH3:12])[CH2:7][CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178501226HCID 178501226, compound

Product 1

HCID 178484819HCID 178484819, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of trans-4-[(tert-Butoxycarbonyl)(methyl)amino]cyclohexanecarboxylic acid methyl ester (3.69 mmol, 1.0 g) is dissolved in EtOAc (5 mL), cooled to 0° C. and treated with 4M HCl in ethyl acetate (5 mL). The mixture is stirred at room temperature for 5 hours. After the mixture is concentrated under reduced pressure, 100 mL of ethyl ether is added. The solid precipitate is filtrated, washed with ethyl ether and dried under reduced pressure to obtain 700 mg (91%) of trans-4-(methylamino)cyclohexanecarboxylic acid methyl ester hydrochloride as white solid. ESI-MS m/z: 171 [M+1]+, Retention time 1.00 min (condition B).

Workup

  1. concentrationAfter the mixture is concentrated under reduced pressure, 100 mL of ethyl ether
  2. additionis added
  3. filtrationThe solid precipitate is filtrated
  4. washwashed with ethyl ether
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-8233d07f943f4936aed422ac2619c5b4
Source dataset
uspto-grants-2014_06
Patent number
US08759365B2

Reaction notes

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