Morpholine → HCID 19753952, compound

HRID 847552Notes

Reaction equation

HRID 847552 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)=[O:15])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 5458485-(((Tert-butoxy)carbonyl)amino)pentanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 19753952HCID 19753952, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 5-(N-t-butoxycarbonylamino)valeric acid (2.173 g) and morpholine (1.045 g) in anhydrous methylene chloride (22 ml) was added N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.30 g) portionwise at 0°-5° C. After being stirred for 3 hours at the same temperature, the solvent was evaporated in vacuo and the residue was dissolved in ethyl acetate (100 ml) and water (100 ml). The organic layer was washed with 0.5 N hydrochloric acid (100 ml), water (100 ml), aqueous sodium bicarbonate (100 ml), water (100 ml) and brine (100 ml) successively, and dried over magnesium sulfate. Evaporation of the solvent gave 4-[5-(N-t-butoxycarbonylamino)valeryl]morpholine (1.668 g) as an oil.

Workup

  1. customthe solvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate (100 ml)
  3. washThe organic layer was washed with 0.5 N hydrochloric acid (100 ml), water (100 ml), aqueous sodium bicarbonate (100 ml), water (100 ml) and brine (100 ml) successively
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-7c8eba5ef38545af95667ef23cfa6858
Source dataset
uspto-grants-1992_08
Patent number
US05142048

Reaction notes

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