Chloroform → 3-(N,N-diethylcarbamyl)-8-methyl-3,8-diazabicyclo[3.2.1]octane monohydrochloride

HRID 268219Notes

Reaction equation

HRID 268219 reaction equation
Cl.Cl.[CH3:3][N:4]1[CH:9]2[CH2:10][CH2:11][CH:5]1[CH2:6][NH:7][CH2:8]2.[OH-].[Na+].C(Cl)(Cl)[Cl:15].[CH2:18]([N:20]([CH2:24][CH3:25])[C:21](Cl)=[O:22])[CH3:19]>O>[ClH:15].[CH2:18]([N:20]([CH2:24][CH3:25])[C:21]([N:7]1[CH2:6][CH:5]2[N:4]([CH3:3])[CH:9]([CH2:10][CH2:11]2)[CH2:8]1)=[O:22])[CH3:19]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 6916Diethylcarbamoyl chlorideHCID 14798Sodium HydroxideHCID 221201898-Methyl-3,8-diazabicyclo(3.2.1)octane dihydrochloride

Product 1

HCID 215454833-(N,N-diethylcarbamyl)-8-methyl-3,8-diazabicyclo[3.2.1]octane monohydrochlorideYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8-Methyl-3,8-diazabicyclo[3.2.1]octane dihydrochloride (2.5 g, 0.0126 mole) was stirred vigorously in a 2-phase system of 20 ml aqueous 10% sodium hydroxide and 50 ml chloroform for 1/2 hour at room temperature. Then at 0°C, 2.56 g (0.0189 mole) diethylcarbamyl chloride was added and the reaction was stirred 18 hours at room temperature. Hot water (50 ml) was added. The solution was extracted twice with chloroform and the extract dried with sodium sulfate. After evaporation, a solution of the oily free base in diethyl ether was treated with ethanolic hydrogen chloride to yield 2.92 g (89% yield) 3-(N,N-diethylcarbamyl)-8 -methyl-3,8-diazabicyclo [3.2.1]octane monohydrochloride, a white solid melting at 202°-205°C.

Workup

  1. extractionThe solution was extracted twice with chloroform
  2. dry with materialthe extract dried with sodium sulfate
  3. customAfter evaporation
  4. additiona solution of the oily free base in diethyl ether was treated with ethanolic hydrogen chloride

Sources & evidence

ORD record
ord-be98a15875704e579178d79b1ce1a1c6
Source dataset
uspto-grants-1976_03
Patent number
US03947445

Reaction notes

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