Sodium Hydroxide → HCID 86736554, compound

HRID 263069Notes

Reaction equation

HRID 263069 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-f837e15a81644a569819c4c21df058e1
Source dataset
uspto-grants-1979_05
Patent number
US04156014

Reaction notes

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