Diethyl Ether → Dicyclohexylamine

HRID 127582Notes

Reaction equation

HRID 127582 reaction equation
[CH:1]1([NH:7][CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(SC[C@@H](C)C(N1[C@H](C(O)=O)CC2C(=CC=CC=2)C1)=O)(=O)C1C=CC=CC=1.CCOCC.CCCCCC>N.CO>[CH:8]1([NH:7][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 8058HexaneHCID 86737594HCID 86737594, compound

Product 1

HCID 7582DicyclohexylamineYield 82.7%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

1.26 g of (3S)-2-[(2S)-3-benzoylthio-2-methylpropionyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid dicyclohexylamine salt are suspended in a mixture of 15 ml of 10 % aqueous ammonia and 5 ml of methanol. The mixture is stirred at room temperature for 3.5 hours in nitrogen gas atmosphere. The reaction mixture is condensed to dryness under reduced pressure, and a mixture of ether and n-hexane is added thereto. Crystalline precipitates are collected by filtration, washed with ether and recrystallized from ethanol. 0.85 g of (3S)-2-[(2S)-3-mercapto-2-methylpropionyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid.dicyclohexylamine salt is thereby obtained as colorless crystals. Yield: 82.7 % M.p. 191°-192° C.(decomp.) (This product begins to gradually decompose at about 172° C.). All the physico-chemical properties of this product are identical with those of the sample obtained in Example 1-(3).

Workup

  1. customcondensed to dryness under reduced pressure
  2. additionis added
  3. customCrystalline precipitates
  4. filtrationare collected by filtration
  5. washwashed with ether
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-f33836363bdc44cba9ffa2e698cc68c7
Source dataset
uspto-grants-1981_03
Patent number
US04256751

Reaction notes

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