m-Tolyl isocyanate → 1-[1-(3,4-dichlorobenzyl)pyrrolidin-3-(RS)-ylmethyl]-3-[1-(naphth-1-yl)ethyl]urea

HRID 1276376Notes

Reaction equation

HRID 1276376 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([Cl:16])[CH:10]=2)[CH2:4]1.CC1C=C(N=C=O)C=CC=1.[C:27]1([CH:37]([N:39]=[C:40]=[O:41])[CH3:38])[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][CH:28]=1>>[Cl:16][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][C:12]=1[Cl:15])[CH2:8][N:5]1[CH2:6][CH2:7][CH:3]([CH2:2][NH:1][C:40]([NH:39][CH:37]([C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=[CH:29][CH:28]=2)[CH3:38])=[O:41])[CH2:4]1

Participants

4

Reactant 3

HCID 69303m-Tolyl isocyanateHCID 6027531-(1-Isocyanatoethyl)naphthaleneHCID 221153103-Aminomethyl-1-(3,4-dichlorobenzyl)pyrrolidine

Product 1

HCID 99556791-[1-(3,4-dichlorobenzyl)pyrrolidin-3-(RS)-ylmethyl]-3-[1-(naphth-1-yl)ethyl]urea

Procedure

Proceeding as described above but substituting 3-(RS)-aminomethyl-1-(3,4-methylenedioxybenzyl)pyrrolidine with 3-aminomethyl-1-(3,4-dichlorobenzyl)-pyrrolidine and 3-methylphenylisocyanate with 1-(naphth-1-yl)ethylisocyanate gave 1-[1-(3,4-dichlorobenzyl)pyrrolidin-3-(RS)-ylmethyl]-3-[1-(naphth-1-yl)ethyl]urea.

Sources & evidence

ORD record
ord-5a0daf6b2618497aacc59e31984ced50
Source dataset
uspto-grants-2000_12
Patent number
US06166015

Reaction notes

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