Triethylamine → HCID 86736554, compound

HRID 2050103Notes

Reaction equation

HRID 2050103 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:10]=[C:11]([CH:22]=[CH:23][C:24]=1[Cl:25])[NH:12][C@@H:13]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]1[NH:20][CH3:21].[OH-].[Na+].Cl[C:29]([O:31][CH2:32][C:33]([Cl:36])([Cl:35])[Cl:34])=[O:30].C(=O)(O)[O-].[Na+]>C(OCC)C>[ClH:8].[Cl:8][C:9]1[CH:10]=[C:11]([CH:22]=[CH:23][C:24]=1[Cl:25])[NH:12][C@@H:13]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]1[N:20]([CH3:21])[C:29]([O:31][CH2:32][C:33]([Cl:36])([Cl:35])[Cl:34])=[O:30]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 870632,2,2-Trichloroethyl chloroformateHCID 516892Sodium BicarbonateHCID 54443796HCID 54443796, compound

Product 1

HCID 86736554HCID 86736554, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a mixture of 3.03 g. (0.03 mole) of triethylamine and 0.03 mole of the free diamine, trans-3,4-dichloro-N-[2-(N-methylamino)cycloheptyl]aniline, released from its hydrochloride salt with sodium hydroxide, in 250 ml. of ethyl ether, there is added 6.36 g. (0.03 mole) of 2,2,2-trichloroethyl chloroformate in 50 ml. of ethyl ether. The mixture is stirred at room temperature for 2 hours. Then 100 ml. of saturated sodium bicarbonate solution is added. The organic layer is dried over magnesium sulfate and concentrated to a yellow oil. This oil is converted to its hydrochloride salt by treatment with excess ethereal hydrochloric acid. This subtitled salt is recrystallized from a mixture of 120 ml. of methanol and 400 ml. of ethyl ether.

Workup

  1. additionTo a mixture of 3.03 g
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. concentrationconcentrated to a yellow oil
  4. customThis subtitled salt is recrystallized from a mixture of 120 ml

Sources & evidence

ORD record
ord-ec32e30125a2427aa5434fe0dff6b916
Source dataset
uspto-grants-1980_04
Patent number
US04199589

Reaction notes

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