Methyl Isocyanate → N-[2-(4-methoxyphenyl)-1-methylethyl]-N-ethyl-[1-(methylaminocarbonyl)piperidin-4-ylmethyl]amine

HRID 429829Notes

Reaction equation

HRID 429829 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([N:12]([CH2:15][CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH2:13][CH3:14])[CH3:11])=[CH:5][CH:4]=1.[CH3:22][N:23]=[C:24]=[O:25]>C(OCC)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH:10]([N:12]([CH2:15][CH:16]2[CH2:21][CH2:20][N:19]([C:24]([NH:23][CH3:22])=[O:25])[CH2:18][CH2:17]2)[CH2:13][CH3:14])[CH3:11])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 18352857N-[2-(4-methoxyphenyl)-1-methylethyl]-N-ethyl-(piperidin-4-ylmethyl)amine

Product 1

HCID 18352862N-[2-(4-methoxyphenyl)-1-methylethyl]-N-ethyl-[1-(methylaminocarbonyl)piperidin-4-ylmethyl]amineYield 91%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of N-[2-(4-methoxyphenyl)-1-methylethyl]-N-ethyl-(piperidin-4-ylmethyl)amine (0.23 grams, 0.79 mmole) in ethyl ether (10 ml) was added methyl isocyanate (0.2 ml, 3.4 mmole). After 1.0 hour at 22° C., the solution was concentrated under reduced pressure and the residue was recrystallized from ethyl ether/hexane to give N-[2-(4-methoxyphenyl)-1-methylethyl]-N-ethyl-[1-(methylaminocarbonyl)piperidin-4-ylmethyl]amine (0.249 grams, 91%) m.p. 97-98° C.

Workup

  1. concentrationthe solution was concentrated under reduced pressure
  2. customthe residue was recrystallized from ethyl ether/hexane

Sources & evidence

ORD record
ord-b0fa2867469341bba7e37178b59ca89c
Source dataset
uspto-grants-2001_11
Patent number
US06319920B1

Reaction notes

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