4-Methylmorpholine → HCID 9952505, compound

HRID 235155Notes

Reaction equation

HRID 235155 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6]O[CH2:4][CH2:3]1.O.O[N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2N=N1.[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH2:25])=[CH:22][CH:21]=1.[C:28](=[O:31])([O-])[O-].[Na+].[Na+]>O.C(Cl)Cl>[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH:25][C:28]([C:13]2[CH:14]=[CH:15][C:18]3[C:13](=[C:14]([N:10]4[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]4)[CH:15]=[CH:16][CH:17]=3)[CH:18]=2)=[O:31])=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 10340Sodium CarbonateHCID 660364-ChlorobenzylamineHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 9952505HCID 9952505, compoundYield 21.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of the above acid (0.25 g, 0.82 mmol), methylene chloride (4 mL), N-methylmorpholine (0.31 mL, 2.87 mmol), 1-hydroxy benzotriazole hydrate (0.12 g, 0.9 mmol), 4-chlorobenzylamine (0.1 mL, 0.82 mmol) and 1-cyclohexyl-3-(7-morpholinoethyl) carbodiimide p-toluenesulfonate (0.69 g, 1.62 mmol) was stirred 17 hours at ambient temperature. The reaction was diluted with water (10 mL) and methylene chloride (10 mL) and adjusted to pH 9 by addition of saturated aqueous sodium carbonate. The phases were separated and the organic layer was dried over sodium sulfate and concentrated to a yellow solid. This material was purified by flash chromatography on silicon gel (6 g). Elution with 12: 1: 0.04, methylene chloride, methanol, ammonium hydroxide gave 0.07 g (21.8%) of the title compound as a solid: mp 72°-74° C.; tic: Rf =0.28 (12: 1: 0.04, methylene chloride, methanol, ammonium hydroxide); 13C NMR δ 168.04, 150.69, 137.09, 136.16, 133.17, 130.82, 129.01, 128.90, 128.77, 128.18, 127.91, 123.84, 123.30, 123.07, 115.61, 55.47, 53.10, 46.13, 43.34. HRMS m/e calculated for C23H24ClN3O: 393.1607. Observed m/e: 393.1642.

Workup

  1. customThe phases were separated
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. concentrationconcentrated to a yellow solid
  4. customThis material was purified by flash chromatography on silicon gel (6 g)
  5. washElution with 12: 1: 0.04, methylene chloride, methanol, ammonium hydroxide

Sources & evidence

ORD record
ord-7e8c58e0baae40bdb955b2f5925eda32
Source dataset
uspto-grants-1997_01
Patent number
US05597826

Reaction notes

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