Triethylamine → HCID 86624311, compound

HRID 1947198Notes

Reaction equation

HRID 1947198 reaction equation
C(N(CC)CC)C.[N:8]1([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.[C:22](Cl)(Cl)=[S:23].[OH-].[Na+]>O1CCCC1>[N:21]([C:18]1[CH:19]=[CH:20][C:15]([CH2:14][N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:16][CH:17]=1)=[C:22]=[S:23]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 14798Sodium HydroxideHCID 7768514-(Morpholinomethyl)aniline

Product 1

HCID 86624311HCID 86624311, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (4.5 mL, 65.4 mmol) was added to a tetrahydrofuran (500 mL) solution of 4-morpholin-4-ylmethyl-phenylamine (F45-000, 5.16 g, 26.8 mmol). After cooling in ice cold, thiophosgene (2.45 mL, 32.1 mmol) was added. After stirring at room temperature overnight, aqueous sodium hydroxide was added until the reaction mixture became basic. The reaction mixture was extracted with ethyl acetate, washed with water and then washed with saturated sodium chloride. The extract solution was dried over anhydrous sodium sulfate, and then sodium sulfate was removed by filtration and the solvent was distilled off under reduced pressure to obtain a red syrup like substance. The syrup like substance was purified by silica gel column chromatography (hexane, ethyl acetate) to obtain 4-(4-isothiocyanatobenzyl)-morpholine (F45-00, brown oil, 5.72 g, 91%).

Workup

  1. temperatureAfter cooling in ice cold
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washwashed with water
  4. washwashed with saturated sodium chloride
  5. dry with materialThe extract solution was dried over anhydrous sodium sulfate
  6. customsodium sulfate was removed by filtration
  7. distillationthe solvent was distilled off under reduced pressure
  8. customto obtain a red syrup like substance
  9. customThe syrup like substance was purified by silica gel column chromatography (hexane, ethyl acetate)

Sources & evidence

ORD record
ord-7096c4e6d5174fd195cce05df51b723d
Source dataset
uspto-grants-2013_03
Patent number
US08399464B2

Reaction notes

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