Hydrochloric Acid → HCID 178483656, compound

HRID 1063643Notes

Reaction equation

HRID 1063643 reaction equation
C(O[C:6]([N:8](C)[CH2:9][CH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([C:17]([OH:19])=[O:18])[CH2:13][CH2:12]1)=O)(C)(C)C.[ClH:21]>O1CCOCC1>[CH3:6][NH:8][CH2:9][CH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([C:17]([OH:19])=[O:18])[CH2:13][CH2:12]1.[ClH:21]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178483658HCID 178483658, compound

Product 1

HCID 178483656HCID 178483656, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
10 °C

Procedure

A solution of 17.24 g (60.4 mmol) of trans-4-[2-(tert-butoxycarbonyl-methyl-amino)-ethyl]-cyclohexanecarboxylic acid was dissolved in 150 mL of dioxane, cooled to 10° C. and treated with 151 mL (604.1 mmol, 10 eq) of 4M HCl in dioxane, then warmed to RT and stirred for 3 h. The solution was evaporated to ca. 15 mL, precipitated with ˜100 mL of Et2O and cooled to 0° C. The solid precipitate was filtrated, washed with Et2O (×3) and dried under reduced pressure to yield 13.55 g (quantitative) of trans-4-(2-methylamino-ethyl)-cyclohexanecarboxylic acid·HCl, MS: 186 (MH+), MP: 212-214° C.

Workup

  1. temperaturewarmed to RT
  2. customThe solution was evaporated to ca. 15 mL
  3. customprecipitated with ˜100 mL of Et2O
  4. temperaturecooled to 0° C
  5. filtrationThe solid precipitate was filtrated
  6. washwashed with Et2O (×3)
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-05b59161e5f848e3b6960401d90fbe96
Source dataset
uspto-grants-2005_11
Patent number
US06965048B2

Reaction notes

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