N-(3-Aminopropyl)morpholine → HCID 25139621, compound

HRID 1669135Notes

Reaction equation

HRID 1669135 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][NH2:10])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl[C:12]1[N:13]=[N+:14]([O-:26])[C:15]2[CH:25]=[C:24]3[C:19]([CH2:20][CH2:21][CH2:22][CH2:23]3)=[CH:18][C:16]=2[N:17]=1>COCCOC>[N:1]1([CH2:7][CH2:8][CH2:9][NH:10][C:12]2[N:13]=[N+:14]([O-:26])[C:15]3[CH:25]=[C:24]4[C:19]([CH2:20][CH2:21][CH2:22][CH2:23]4)=[CH:18][C:16]=3[N:17]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 61055N-(3-Aminopropyl)morpholineHCID 25139620HCID 25139620, compound

Product 1

HCID 25139621HCID 25139621, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

3-(4-Morpholinyl)propylamine (314 mg, 2.18 mmol) was added to a stirred solution of chloride 176 (171 mg, 0.73 mmol) in DME (8 mL) and the solution stirred at reflux temperature for 30 min. The solution was cooled and partitioned in between EtOAc and aqueous Na2CO3 solution. The organic fraction was washed with water, dried and the solvent evaporated to give 1-oxide 179 (250 mg, 100%) as an orange solid: mp (EtOAc) 115-116° C.; 1H NMR δ 7.97 (s, 1H, H-10), 7.29 (s, 1H, H-5), 6.14 (br s, 1H, NH), 3.75 (t, J=4.6 Hz, 4H, 2×CH2O), 3.60 (q, J=6.2 Hz, 2H, CH2N), 2.86-2.95 (m, 4H, H-6, H-9), 2.45-2.56 (m, 6H, 3×CH2N), 1.80-1.88 (m, 6H, H-7, H-8, CH2); 13C NMR δ 158.7, 147.5 147.0, 136.0, 129.1, 124.9, 119.0, 67.0 (2), 57.3, 53.8 (2), 40.8, 30.0, 29.3, 25.3, 22.7, 22.5. Anal. calcd for C18H25N5O2: C, 63.0; H, 7.3; N, 20.4. Found: C, 62.8; H, 7.4; N, 20.3%.

Workup

  1. temperatureat reflux temperature for 30 min
  2. temperatureThe solution was cooled
  3. custompartitioned in between EtOAc and aqueous Na2CO3 solution
  4. washThe organic fraction was washed with water
  5. customdried
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-d66bb5f18d02498a8326d1e4809e0104
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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