N-(3-Aminopropyl)morpholine → HCID 25140918, compound

HRID 1669156Notes

Reaction equation

HRID 1669156 reaction equation
Cl[C:2]1[N:3]=[N+:4]([O-:15])[C:5]2[CH:11]=[C:10]3[CH2:12][CH2:13][O:14][C:9]3=[CH:8][C:6]=2[N:7]=1.[N:16]1([CH2:22][CH2:23][CH2:24][NH2:25])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1>COCCOC>[N:16]1([CH2:22][CH2:23][CH2:24][NH:25][C:2]2[N:3]=[N+:4]([O-:15])[C:5]3[CH:11]=[C:10]4[CH2:12][CH2:13][O:14][C:9]4=[CH:8][C:6]=3[N:7]=2)[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 61055N-(3-Aminopropyl)morpholineHCID 25139754HCID 25139754, compound

Product 1

HCID 25140918HCID 25140918, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of chloride 206 (250 mg, 1.1 mmol) and 3-(4-morpholinyl)propylamine (0.65 mL, 4.5 mmol) in DME (25 mL) was stirred at reflux temperature for 2 h, the solvent evaporated and the residue purified by chromatography, eluting with a gradient (2-5%) of MeOH/DCM, to give 1-oxide 211 (340 mg, 92%) as a yellow solid: mp 152-154° C.; 1H NMR δ 8.10 (t, J=1.6 Hz, 1H, H-9), 6.79 (s, 1H, H-5), 6.09 (br s, 1H, NH), 4.42 (t, J=8.3 Hz, 2H, H-7), 3.75 (t, J=4.7 Hz, 4H, 2×CH2O), 3.55-3.60 (m, 2H, CH2), 3.30 (dt, J=8.3, 1.6 Hz, 2H, H-7), 2.46-2.52 (m, 6H, 2×CH2N, CH2), 1.82 (p, J=6.5 Hz, 2H, CH2); 13C NMR δ 166.5, 159.4, 151.8, 129.2, 126.4, 116.6, 102.1, 72.9, 67.0 (2), 57.3, 53.8 (2), 40.8, 28.6, 25.3. Anal. calcd for C16H21N5O3: C, 58.0; H, 6.4; N, 21.1. Found: C, 57.8; H, 6.2; N, 21.1%.

Workup

  1. temperatureat reflux temperature for 2 h
  2. customthe solvent evaporated
  3. customthe residue purified by chromatography
  4. washeluting with a gradient (2-5%) of MeOH/DCM

Sources & evidence

ORD record
ord-af9f2fd372aa48f8ba45bf13950faba9
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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