Diethyl Ether → HCID 178511263, compound

HRID 1906398Notes

Reaction equation

HRID 1906398 reaction equation
[NH2:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1.O.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16](S(O)(=O)=O)=[CH:15][CH:14]=1.O.C1(C)C(S(O)(=O)=O)=CC=CC=1.CCOCC>C(O)C1C=CC=CC=1.C1(C)C=CC=CC=1>[CH2:23]([O:10][C:9]([C@H:6]1[CH2:5][CH2:4][C@H:3]([CH2:2][NH2:1])[CH2:8][CH2:7]1)=[O:11])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 521998p-Toluenesulfonic acid monohydrateHCID 124969952-Methylbenzenesulfonic acid hydrateHCID 178511262HCID 178511262, compound

Product 1

HCID 178511263HCID 178511263, compoundYield 145.2%

Reagents, catalysts & solvents 2

HCID 244Benzyl AlcoholSolventHCID 1140TolueneSolvent

Procedure

Trans-4-Aminomethyl cyclohexane carboxylic acid (25 g; 160 mmol) in benzyl alcohol (100 cm3) and toluene (50 cm3) with para-toluene sulphonic acid monohydrate (30.2 g; 1 equivalent) was refluxed for 171/2 hours using a Dean and Stark apparatus to collect the water of condensation and from the toluene sulphonic acid monohydrate. The clear reaction mixture was poured into ether (600 cm3) and the resultant white solid filtered off, washed with ether and dried to afford 57 g (85%) of the title compound. Both infrared and nuclear magnetic resonance spectra were consistant with the desired compound.

Workup

  1. customto collect
  2. customthe water of condensation
  3. filtrationthe resultant white solid filtered off
  4. washwashed with ether
  5. customdried

Sources & evidence

ORD record
ord-a3f1a3185dce42fbbfdf63572b0b2eaf
Source dataset
uspto-grants-1987_03
Patent number
US04652560

Reaction notes

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