Potassium Carbonate → Ethyl 1-(3-ethoxycarbonylpropylamino)cyclohexanecarboxylate

HRID 975838

Reaction equation

HRID 975838 reaction equation
[NH2:1][C:2]1([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>>[CH2:26]([O:25][C:23]([CH2:22][CH2:21][CH2:20][NH:1][C:2]1([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1)=[O:24])[CH3:27]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 222863Ethyl 1-aminocyclohexanecarboxylate

Product 1

HCID 13282875Ethyl 1-(3-ethoxycarbonylpropylamino)cyclohexanecarboxylate

Conditions

Temperature
130 °C

Procedure

A mixture of ethyl 1-aminocyclohexanecarboxylate (669 g), potassium carbonate (683.1 g) and ethyl 4-bromobutyrate (558 ml) was stirred at 130° C. for 18 hours, then cooled to ambient temperature and poured onto ice-water (3 l). The product was extracted into dichloromethane and the combined extracts were dried over sodium sulphate and the solvent was removed in vacuo to yield ethyl 1-(3-ethoxycarbonylpropylamino)cyclohexanecarboxylate as a brown/orange oil. Yield 943.2 g.

Workup

  1. temperaturecooled to ambient temperature
  2. additionpoured onto ice-water (3 l)
  3. extractionThe product was extracted into dichloromethane
  4. dry with materialthe combined extracts were dried over sodium sulphate
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-40fb88ba0f324bcc8f0a527c3d225990
Source dataset
uspto-grants-1997_03
Patent number
US05610161

Linked notes

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