Triethylamine → HCID 86736570, compound

HRID 237016Notes

Reaction equation

HRID 237016 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[Cl:18])[NH:5][C@@H:6]1[CH2:10][CH2:9][CH2:8][C@H:7]1[NH:11][CH2:12][CH:13]=[CH2:14].C(N(CC)CC)C.Cl[C:27]([O:29][CH2:30][C:31]([Cl:34])([Cl:33])[Cl:32])=[O:28].C(=O)(O)[O-].[Na+]>C(OCC)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[Cl:18])[NH:5][C@@H:6]1[CH2:10][CH2:9][CH2:8][C@H:7]1[N:11]([CH2:12][CH:13]=[CH2:14])[C:27]([O:29][CH2:30][C:31]([Cl:34])([Cl:33])[Cl:32])=[O:28]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 870632,2,2-Trichloroethyl chloroformateHCID 516892Sodium BicarbonateHCID 54279576HCID 54279576, compound

Product 1

HCID 86736570HCID 86736570, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a mixture of 17.9 g (0.05 mole) of the above trans-3,4-dichloro-N-[2-(N-allylamino)cyclopentyl]-aniline, released from its hydrochloride salt and 5.5 g (0.05 mole) of triethylamine in 400 ml of ethyl ether there was added dropwise 10.6 g (0.05 mole) of 2,2,2-trichloroethyl chloroformate in 50 ml of ethyl ether while cooling the reaction vessel in ice in 30 minutes. The mixture was then stirred overnight at room temperature. The next day 250 ml of saturated sodium bicarbonate solution was added. The organic layer was then separated and washed with saturated sodium chloride solution, dried over magnesium sulfate and evaporated to a yellow oil, weighing 23.0 g. This was the crude sub-titled amine. A 1.0 g portion of this amine oil was converted to its hydrochloride salt with excess ethereal hydrogen chloride and the salt was recrystallized from a mixture of 15 ml of methanol and 80 ml of ethyl ether to obtain the trans-3,4-dichloro-N-[2-(N-allyl-N-trichloroethoxycarbonylamino)cyclopentyl]aniline hydrochloride, m.p. 160°-162° C., softens, then melts.

Workup

  1. temperaturewhile cooling the reaction vessel in ice in 30 minutes
  2. customThe organic layer was then separated
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to a yellow oil
  6. customthe salt was recrystallized from a mixture of 15 ml of methanol and 80 ml of ethyl ether

Sources & evidence

ORD record
ord-1c2fe624bc6f48beae1f4e546682f76c
Source dataset
uspto-grants-1979_06
Patent number
US04159340

Reaction notes

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