Ethyl chloroformate → HCID 21482171, compound

HRID 1415399Notes

Reaction equation

HRID 1415399 reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:22][C:23]2[S:27][CH:26]=[CH:25][CH:24]=2)[CH2:9]1)C1C=CC=CC=1.Cl[C:29]([O:31][CH2:32][CH3:33])=[O:30]>C1(C)C=CC=CC=1>[CH2:32]([O:31][C:29]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:22][C:23]2[S:27][CH:26]=[CH:25][CH:24]=2)[CH2:9]1)=[O:30])[CH3:33]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 136824814-Benzyl-2-({2-[(thiophen-2-yl)methyl]phenoxy}methyl)morpholine

Product 1

HCID 21482171HCID 21482171, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3.8 g of 4-benzyl-2-[2-(2-thenyl)phenoxymethyl]-morpholine in 30 ml of toluene was added 1.2 g of ethyl chloroformate, and the mixture was heated under reflux for 6 hours. After cooling, the insoluble material was filtered off and the filtrate was concentrated under reduced pressure to give 3.1 g of crude 4-ethoxycarbonyl-2-[2-(2-thenyl)-phenoxymethyl]morpholine as an oil. The oil was dissolved in 40 ml of ethanol, and a solution of 3.2 g of barium hydroxide in 50 ml of water was added, and the mixture was heated under reflux for 8 hours. After cooling, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The remaining oil was extracted with two 70 ml portions of 5% hydrochloric acid, and the combined water layer was made alkaline with sodium hydroxide. The liberated oil was extracted with benzene, and the benzene extract was dried over potassium carbonate. Then the benzene was distilled off to give 1.6 g of 2-[2-(2-thenyl)phenoxymethyl]-morpholine as an oil. A solution of the oil (1.6 g) in 15 ml of isopropyl ether was added to a solution of 0.65 g of maleic acid in 7 ml of ethanol to give 2.1 g of colorless crystals. The crystals were recrystallized from a mixture of methanol and isopropyl ether (1:1) to give 1.5 g of 2-[2-(2-thenyl)phenoxymethyl]morpholine maleate as colorless crystals, melting at 155°-156° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 6 hours
  3. temperatureAfter cooling
  4. filtrationthe insoluble material was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9ed762bdcb584d8e9510033c6d5fbd2d
Source dataset
uspto-grants-1977_01
Patent number
US04005084

Reaction notes

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