Morpholine → HCID 178501151, compound

HRID 1820925Notes

Reaction equation

HRID 1820925 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]([OH:13])=O)[CH2:7][CH2:6]1)=[O:4].[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>C(Cl)(Cl)Cl>[N:14]1([C:11]([C@H:8]2[CH2:7][CH2:6][C@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:10][CH2:9]2)=[O:13])[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178501163HCID 178501163, compound

Product 1

HCID 178501151HCID 178501151, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

trans-4-(Methoxycarbonyl)cyclohexanecarboxylic acid (800 mg) obtained in Reference Example 1(2) is dissolved in chloroform (30 ml), and thereto are added morpholine (560 mg), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (1.24 g) and triethylamine (650 mg) under ice-cooling. The mixture is then stirred at room temperature for 19 hours. Ice-water is poured to the reaction solution and the mixture is extracted with chloroform. The organic layer is washed successively with 10% hydrochloric acid, a saturated aqueous sodium hydrogen carbonate solution and saturated brine and dried over sodium sulfate. The solvent is concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (eluent: chloroform, then chloroform/methanol=30/1) to give methyl trans-4-(morpholin-4-ylcarbonyl)cyclohexanecarboxylate (897 mg).

Workup

  1. temperaturecooling
  2. extractionthe mixture is extracted with chloroform
  3. washThe organic layer is washed successively with 10% hydrochloric acid
  4. dry with materiala saturated aqueous sodium hydrogen carbonate solution and saturated brine and dried over sodium sulfate
  5. concentrationThe solvent is concentrated under reduced pressure
  6. customThe resulting residue is purified by silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-c11e8dc9448d4ab68a3234161efc6769
Source dataset
uspto-grants-2009_10
Patent number
US07605158B2

Reaction notes

Loading…