Ethyl isocyanate → N-ethyl-8-methyl-3,8-diazabicyclo[3.2.1]octane-3-carboxamide

HRID 1605940Notes

Reaction equation

HRID 1605940 reaction equation
Cl.Cl.CN1C2CCC1CNC2.C(N=C=O)C.[CH2:17]([N:19](CC)[C:20]([N:22]1[CH2:28][CH:27]2[N:29]([CH3:30])[CH:24]([CH2:25][CH2:26]2)[CH2:23]1)=[O:21])[CH3:18]>>[CH2:17]([NH:19][C:20]([N:22]1[CH2:28][CH:27]2[N:29]([CH3:30])[CH:24]([CH2:25][CH2:26]2)[CH2:23]1)=[O:21])[CH3:18]

Participants

4

Reactant 3

HCID 8022Ethyl isocyanateHCID 423352N,N-diethyl-8-methyl-3,8-diazabicyclo[3.2.1]octane-3-carboxamideHCID 221201898-Methyl-3,8-diazabicyclo(3.2.1)octane dihydrochloride

Product 1

HCID 423351N-ethyl-8-methyl-3,8-diazabicyclo[3.2.1]octane-3-carboxamideYield 79%

Procedure

8-Methyl-3,8-diazabicyclo[3.2.1]octane dihydrochloride (2.5 g, 0.0126 mole), prepared as described in Example 1, was reacted with 2.0 ml (0.0253 mole) ethyl isocyanate according to the procedure described above for 3-(N,N-diethylcarbamyl)-8-methyl-3,8-diazabicyclo[3.2.1]octane in Example 1. A white monohydrochloride, melting point 246°-250° C (dec.) was obtained in 79% yield: 2.33 g.

Sources & evidence

ORD record
ord-c968453acb8a4c0bb8511e4b7744a698
Source dataset
uspto-grants-1976_04
Patent number
US03951980

Reaction notes

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