Sodium Hydroxide → HCID 86736554, compound

HRID 237013Notes

Reaction equation

HRID 237013 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[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C@H:7]1[NH:13][CH3:14].[OH-].[Na+].Cl[C:22]([O:24][CH2:25][C:26]([Cl:29])([Cl:28])[Cl:27])=[O:23].C(=O)(O)[O-].[Na+]>C(OCC)C.C(N(CC)CC)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[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C@H:7]1[N:13]([CH3:14])[C:22]([O:24][CH2:25][C:26]([Cl:29])([Cl:28])[Cl:27])=[O:23]

Participants

7

Reactant 4

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

Product 1

HCID 86736554HCID 86736554, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a mixture of equimolar quantities of triethylamine and the free diamine, trans-3,4-dichloro-N-[2-(N-methylamino)cycloheptyl]-aniline, released from its hydrochloride salt with sodium hydroxide, in ethyl ether, there is added an equimolar amount of 2,2,2-trichloroethyl chloroformate in ethyl ether. The mixture is stirred at room temperature for 2 hours. Then saturated sodium bicarbonate solution is added. The organic layer is dried over magnesium sulfate and concentrated to an oil. This oil is converted to its hydrochloride salt by treatment with excess ethereal hydrochloric acid. This sub-titled salt is recrystallized from a mixture of methanol and ethyl ether.

Workup

  1. dry with materialThe organic layer is dried over magnesium sulfate
  2. concentrationconcentrated to an oil
  3. customThis sub-titled salt is recrystallized from a mixture of methanol and ethyl ether

Sources & evidence

ORD record
ord-c4e84c2bb393455e99eda5b9f36c48d4
Source dataset
uspto-grants-1979_06
Patent number
US04159339

Reaction notes

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