N-Aminomorpholine → HCID 67048152, compound

HRID 606363Notes

Reaction equation

HRID 606363 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:18][N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1>CN(C)C=O.CO.C(Cl)Cl.CCN(CC)CC>[N:19]1([NH:18][C:13](=[O:15])[C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:17][CH:16]=2)[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1

Participants

9

Reactant 4

HCID 20315N-AminomorpholineHCID 738804-(Benzyloxy)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 67048152HCID 67048152, compoundYield 92.4%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 4-benzyloxybenzoic acid (0.5 g, 2.19 mmol), 4-aminomorpholine (0.2 mL, 2.13 mmol), Et3N (0.316 mL), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.671 g, 3.5 mmol) and 1-hydroxybenzotriazole hydrate (0.5 g, 3.7 mmol) in N,N-dimethylformamide (17 mL) was stirred at room temperature for 2 days. The reaction was concentrated and diluted in dichloromethane. The organic phase was washed twice with water, dried with MgSO4 and concentrated. The residue was purified on column chromatography (silica gel, 5% MeOH in CH2Cl2) and N-(4-morpholinyl)-4-(phenylmethoxy)-benzamide (0.615 g, yield: 90%) was identified by NMR spectroscopy.

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted in dichloromethane
  3. washThe organic phase was washed twice with water
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e50cf13ed6194a20aa5d043132da2a98
Source dataset
uspto-grants-2011_03
Patent number
US07915295B2

Reaction notes

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