Triethylamine → HCID 12862642, compound

HRID 263131Notes

Reaction equation

HRID 263131 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:10]=[C:11]([CH:20]=[CH:21][C:22]=1[Cl:23])[NH:12][C@@H:13]1[CH2:17][CH2:16][CH2:15][C@H:14]1[NH:18][CH3:19].[OH-].[Na+].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:8].[Cl:8][C:9]1[CH:10]=[C:11]([CH:20]=[CH:21][C:22]=1[Cl:23])[NH:12][C@@H:13]1[CH2:17][CH2:16][CH2:15][C@H:14]1[N:18]([CH3:19])[C:27]([O:29][CH2:30][C:31]([Cl:34])([Cl:33])[Cl:32])=[O:28]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 870632,2,2-Trichloroethyl chloroformateHCID 516892Sodium BicarbonateHCID 12862640HCID 12862640, compound

Product 1

HCID 12862642HCID 12862642, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a mixture of 3.03 g. (0.03 mole) of triethylamine and 9.96 g. (0.03 mole) of the free diamine, trans-3,4-dichloro-N-[2-(N-methylamino)cyclopentyl]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 salt is recrystallized from a mixture of 120 ml. of methanol and 400 ml. of ethyl ether. The subtitled salt weighs 11.25 g. (80% yield). The NMR, IR, UV and mass spectral data are consistent with the subtitled structure.

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 salt is recrystallized from a mixture of 120 ml

Sources & evidence

ORD record
ord-6995a0b3418f40b1afc994cfbedaf5bb
Source dataset
uspto-grants-1979_05
Patent number
US04156015

Reaction notes

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