Diethyl Ether → HCID 13020484, compound

HRID 2198520Notes

Reaction equation

HRID 2198520 reaction equation
Cl.[CH:2]1([CH2:15][C:16]([O:18]CC)=O)[C:7]2[NH:8][C:9]3[C:14]([C:6]=2[CH2:5][CH2:4][NH:3]1)=[CH:13][CH:12]=[CH:11][CH:10]=3.[O-:21][C:22]#[N:23].[Na+].[CH3:25]COCC>O>[CH3:25][N:23]1[C:16](=[O:18])[CH2:15][CH:2]2[C:7]3[NH:8][C:9]4[C:14]([C:6]=3[CH2:5][CH2:4][N:3]2[C:22]1=[O:21])=[CH:13][CH:12]=[CH:11][CH:10]=4

Participants

5

Reactant 3

HCID 3283Diethyl Ether2×HCID 517096Sodium CyanateHCID 20519381Ethyl (2,3,4,9-tetrahydro-1H-beta-carbolin-1-yl)acetate--hydrogen chloride (1/1)

Product 1

HCID 13020484HCID 13020484, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

26 g (0.088 mol) of ethyl 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-acetate hydrochloride are dissolved in 1 liter of hot water. The pH should be 4-5. When the temperature of the reaction medium is 50° C., a solution of 8.7 g (0.13 mol) of sodium cyanate in 150 cm3 of water is added. The reaction medium is kept at 50° C., whilst stirring. It is stirred for 4 hours at 50° C. and left to stand overnight at ambient temperature; the supernatant water is drawn off. 200 cm3 of ether are added, the mixture is stirred, the ether solution is then drawn off and the same operation is repeated. The expected product is very soluble in ether. The ether extracts are combined and washed with acidified water, in order to remove traces of the starting material, and then with water. They are dried over Na2SO4 and the solvent is evaporated off. This yields an oil which changes into a foam on more thorough drying. The product is used as such in the following step.

Workup

  1. customis 50° C.
  2. customis kept at 50° C.
  3. stirringIt is stirred for 4 hours at 50° C.
  4. waitleft
  5. stirringthe mixture is stirred

Sources & evidence

ORD record
ord-38cb2051bbe54cafbf743a4aff7f164f
Source dataset
uspto-grants-1982_11
Patent number
US04358451

Reaction notes

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