Morpholine → HCID 178520992, compound

HRID 645801Notes

Reaction equation

HRID 645801 reaction equation
[OH:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([OH:10])=O)[CH2:4][CH2:3]1.ON1C2N=CC=CC=2N=N1.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>ClCCl>[N:21]1([C:8]([C@@H:5]2[CH2:4][CH2:3][C@H:2]([OH:1])[CH2:7][CH2:6]2)=[O:10])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 181649HOAtHCID 178525779HCID 178525779, compound

Product 1

HCID 178520992HCID 178520992, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of cis-4-hydroxycyclohexanecarboxylic acid (720 mg, 0.5 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimde hydrochloride (1.33 g, 6 mmol) and 1-hydroxy-7-azabenzotriazole (816 mg, 6 mmol) in dichloromethane (6 ml) was treated with morpholine 1.3 ml, 15 mmol). After stirring at room temperature for 18 hours, the crude reaction was applied to a SCX ion exchange cartridge (Varian bond-elute, 5 g) and washed with methanol and then a mixture of 0.880 ammonia:methanol (1:9). The combined basic fractions were concentrated in vacuo, and the resulting residue was purified by column chromatography eluting with a mixture of 0.880 ammonia:ethanol:dichloromethane (1:9:90) to afford the title compound (D55); MS (ES+) m/e 214 [M+H]+.

Workup

  1. customthe crude reaction
  2. washwashed with methanol
  3. additiona mixture of 0.880 ammonia:methanol (1:9)
  4. concentrationThe combined basic fractions were concentrated in vacuo
  5. customthe resulting residue was purified by column chromatography
  6. washeluting with a mixture of 0.880 ammonia:ethanol:dichloromethane (1:9:90)

Sources & evidence

ORD record
ord-cb6c077c693e4d64aff5425d0e54bde4
Source dataset
uspto-grants-2010_04
Patent number
US07704994B2

Reaction notes

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