2-Morpholinoethylamine → N-[2-[4-[[4-(2-oxazolyl)phenyl]methyl]phenoxy)ethyl]-4-morpholineethanamine

HRID 630364

Reaction equation

HRID 630364 reaction equation
[N:1]1([CH2:7][CH2:8][NH2:9])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.I[CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[O:28][CH:29]=[CH:30][N:31]=3)=[CH:23][CH:22]=2)=[CH:16][CH:15]=1>ClCCl>[O:28]1[CH:29]=[CH:30][N:31]=[C:27]1[C:24]1[CH:23]=[CH:22][C:21]([CH2:20][C:17]2[CH:16]=[CH:15][C:14]([O:13][CH2:12][CH2:11][NH:9][CH2:8][CH2:7][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)=[CH:19][CH:18]=2)=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 4082852-MorpholinoethylamineHCID 684895932-[4-[[4-(2-Iodoethoxy)phenyl]methyl]phenyl]oxazole

Product 1

HCID 68488020N-[2-[4-[[4-(2-oxazolyl)phenyl]methyl]phenoxy)ethyl]-4-morpholineethanamineYield 86.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(4-morpholinyl)ethanamine (1 g, 7.4 mmol) in dichloromethane was stirred as a solution of 2-[4-[[4-(2-iodoethoxy)phenyl]methyl]phenyl]oxazole (0.3 g, 0.74 mmol) in dichloromethane was added dropwise and the reaction was heated at reflux for 17 hours. The reaction was concentrated. The residue was dissolved in ethyl acetate and washed with water. The combined organic layers were dried and concentrated. Purification by chromatography on silica gel using a gradient of methanol in dichloromethane gave 0.26 g of N-[2-[4-[[4-(2-oxazolyl)phenyl]methyl]phenoxy]ethyl]-4-morpholineethanamine; 1H NMR (400 MHz, CDCl3) δ 7.97 (d, 2H), 7.68 (s, 1H), 7.27 (d, 2H), 7.21 (s, 1H), 7.13 (d, 2H), 6.82 (d, 2H), 4.08 (t, 2H), 3.96 (s, 2H), 3.67 (m, 4H), 3.03 (t, 2H), 2.78 (t, 2H), 2.51 (t, 2H), 2.43 (m, 4H) ppm.

Workup

  1. additionwas added dropwise
  2. temperaturethe reaction was heated
  3. temperatureat reflux for 17 hours
  4. concentrationThe reaction was concentrated
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with water
  7. customThe combined organic layers were dried
  8. concentrationconcentrated
  9. customPurification by chromatography on silica gel using a gradient of methanol in dichloromethane

Sources & evidence

ORD record
ord-8075f9f261a34d23ab92d3c4414aad8c
Source dataset
uspto-grants-2016_04
Patent number
US09315509B2

Linked notes

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