Ethanol → Dicyclohexylamine

HRID 1249028Notes

Reaction equation

HRID 1249028 reaction equation
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH:3]([C:14]([OH:16])=[O:15])[NH:2]1.[CH:17]1(NC2CCCCC2)[CH2:22]CCC[CH2:18]1.C(O)C.C(I)CC.[C:37](=[S:39])=[S:38]>>[CH:11]1([NH:12][CH:13]2[CH2:5][CH2:4][CH2:3][CH2:14][CH2:1]2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[CH2:18]([S:39][C:37]([N:2]1[CH:3]([C:14]([OH:16])=[O:15])[CH2:4][C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[NH:12][C:13]=2[CH2:1]1)=[S:38])[CH2:17][CH3:22]

Participants

7

Reactant 5

HCID 702EthanolHCID 6348Carbon DisulfideHCID 7582DicyclohexylamineHCID 336431-IodopropaneHCID 982851,2,3,4-Tetrahydro-Beta-Carboline-3-Carboxylic Acid

Product 2

HCID 7582DicyclohexylamineHCID 13561929HCID 13561929, compound

Procedure

To a mixture of (3RS)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (4.32 g), dicyclohexylamine (7.3 g) and 50% ethanol (55 ml) is added dropwise carbon disulfide (1.2 ml). The mixture is stirred at room temperature for 30 minutes, and thereto is added dropwise n-propyl iodide (3.4 g). The mixture is further stirred at room temperature for 10 minutes. The reaction mixture is distilled to remove the solvent. The resulting precipitates are collected by filtration and washed with ether to give dicyclohexylamine salt of the title compound. This product is treated with 10% HCl to give the title compound (4.6 g, 69%) as colorless needles, m.p. 180° C. (decomp.) (recrystallized from ethanol).

Workup

  1. stirringThe mixture is further stirred at room temperature for 10 minutes
  2. distillationThe reaction mixture is distilled
  3. customto remove the solvent
  4. customThe resulting precipitates
  5. filtrationare collected by filtration
  6. washwashed with ether

Sources & evidence

ORD record
ord-f6a71cf185dc4000b58f5720dce3a4c2
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Reaction notes

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