Hydrochloric Acid → 4-Aminotetrahydro-2H-pyran-4-carboxylic acid ethyl ester

HRID 2288105Notes

Reaction equation

HRID 2288105 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([N:12]=C(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].Cl>C(OCC)C>[CH2:1]([O:3][C:4]([C:6]1([NH2:12])[CH2:7][CH2:8][O:9][CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 545353934-[N-(diphenylmethylene)amino]tetrahydropyran-4-carboxylic acid ethyl ester

Product 1

HCID 544950714-Aminotetrahydro-2H-pyran-4-carboxylic acid ethyl esterYield 87.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 4-[N-(diphenylmethylene)amino]tetrahydropyran-4-carboxylic acid ethyl ester (16.0 grams, 0.047 mole) in diethyl ether (120 mL) was added 1M aqueous hydrochloric acid solution (100 mL). The mixture was stirred vigorously at room temperature for 16 hours. The layers were separated and the aqueous layer washed with diethyl ether. The aqueous layer was brought to pH 10 with dilute aqueous ammonium hydroxide solution and extracted with dichloromethane. The organic extract was dried over sodium sulfate and concentrated to give 4-aminotetrahydropyran-4-carboxylic acid ethyl ester (7.128 g, 71.7%) as an oil.

Workup

  1. customThe layers were separated
  2. washthe aqueous layer washed with diethyl ether
  3. extractionextracted with dichloromethane
  4. extractionThe organic extract
  5. dry with materialwas dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-006e6c7fd2884c88aaa00e10bfeecd26
Source dataset
uspto-grants-2000_07
Patent number
US06087392

Reaction notes

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