Oxalic Acid → HCID 131719717, compound

HRID 1779646Notes

Reaction equation

HRID 1779646 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:7]2[CH:8]=[CH:9][NH:10][C:11]=2[CH:12]=[CH:13][CH:14]=1.[CH2:15]1[CH2:24][O:23][C:22]2[CH:21]=[CH:20][C:19]([CH:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)=[CH:18][C:17]=2[O:16]1.[C:31]([OH:36])(=[O:35])[C:32]([OH:34])=[O:33]>C(OCC)(=O)C>[C:31]([OH:36])(=[O:35])[C:32]([OH:34])=[O:33].[NH:10]1[C:11]2[C:7](=[C:6]([O:5][CH2:4][CH2:3][CH2:2][N:28]3[CH2:27][CH2:26][CH:25]([C:19]4[CH:20]=[CH:21][C:22]5[O:23][CH2:24][CH2:15][O:16][C:17]=5[CH:18]=4)[CH2:30][CH2:29]3)[CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:9]1

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 116941694-(3-chloropropoxy)-1H-indoleHCID 15839406HCID 15839406, compound

Product 1

HCID 131719717HCID 131719717, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

The title compound was prepared in similar fashion from 1-chloro-3-(1H-indole-4-oxy)propane and 4-(3,4-ethylenedioxyphenyl)piperidine. The resulting free base was dissolved in ethyl acetate, and precipitated with one equivalent of oxalic acid in ethyl acetate in 59% overall yield as a foam. FDMS m/e=392 (M+ of free base).

Workup

  1. customoverall yield as a foam

Sources & evidence

ORD record
ord-dfca166dbf6c457fa11bea5fa3ec44dc
Source dataset
uspto-grants-1997_05
Patent number
US05627196

Reaction notes

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