Benzo-1,3-dioxole-5-acetic acid → N-[1-(3,4-methylenedioxybenzyl)pyrrolidin-3-(RS)-ylmethyl]-2-(3,4-methylenedioxyphenyl)acetamide

HRID 1276372Notes

Reaction equation

HRID 1276372 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][C:11]([OH:13])=O)=[CH:4][C:3]=2[O:2]1.NCC1CCN(CC2C=CC(Cl)=C(Cl)C=2)C1.[NH2:30][CH2:31][CH:32]1[CH2:36][CH2:35][N:34]([CH2:37][C:38]2[CH:43]=[CH:42][C:41]3[O:44][CH2:45][O:46][C:40]=3[CH:39]=2)[CH2:33]1>>[CH2:45]1[O:44][C:41]2[CH:42]=[CH:43][C:38]([CH2:37][N:34]3[CH2:35][CH2:36][CH:32]([CH2:31][NH:30][C:11](=[O:13])[CH2:10][C:5]4[CH:6]=[CH:7][C:8]5[O:9][CH2:1][O:2][C:3]=5[CH:4]=4)[CH2:33]3)=[CH:39][C:40]=2[O:46]1

Participants

4

Reactant 3

HCID 76115Benzo-1,3-dioxole-5-acetic acidHCID 221153103-Aminomethyl-1-(3,4-dichlorobenzyl)pyrrolidineHCID 221153373-Aminomethyl-1-(3,4-methylenedioxybenzyl)pyrrolidine

Product 1

HCID 9865509N-[1-(3,4-methylenedioxybenzyl)pyrrolidin-3-(RS)-ylmethyl]-2-(3,4-methylenedioxyphenyl)acetamide

Procedure

Proceeding as described above but substituting 4-(2,5-dimethylphenyl)-4-oxobutyric acid with 2-(3,4-methylenedioxyphenyl)acetic acid and 3-aminomethyl-1-(3,4-dichlorobenzyl)pyrrolidine with 3-aminomethyl-1-(3,4-methylenedioxybenzyl)pyrrolidine gave N-[1-(3,4-methylenedioxybenzyl)pyrrolidin-3-(RS)-ylmethyl]-2-(3,4-methylenedioxyphenyl)acetamide.

Sources & evidence

ORD record
ord-073b5e6039df4c24a8f6c15f87ae8c33
Source dataset
uspto-grants-2000_12
Patent number
US06166015

Reaction notes

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