Oxalic Acid → HCID 131719716, compound

HRID 1779645Notes

Reaction equation

HRID 1779645 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.[NH:15]1[CH2:20][CH2:19][C:18]2([CH:25]3[CH2:26][CH:27]=[CH:28][CH:29]=[C:24]3[CH2:23][O:22][CH2:21]2)[CH2:17][CH2:16]1.[C:30]([OH:35])(=[O:34])[C:31]([OH:33])=[O:32]>C(OCC)(=O)C>[C:30]([OH:35])(=[O:34])[C:31]([OH:33])=[O:32].[NH:10]1[C:11]2[C:7](=[C:6]([O:5][CH2:4][CH2:3][CH2:2][N:15]3[CH2:16][CH2:17][C:18]4([CH:25]5[CH2:26][CH:27]=[CH:28][CH:29]=[C:24]5[CH2:23][O:22][CH2:21]4)[CH2:19][CH2:20]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 21268253HCID 21268253, compound

Product 1

HCID 131719716HCID 131719716, 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 1,5-dihydrospiro[4H-2-benzopyran-4,4'-piperidine]. The resulting free base was dissolved in ethyl acetate, and precipitated with one equivalent of oxalic acid in ethyl acetate in 69% overall yield as a foam. FDMS m/e=376 (M+ of free base).

Workup

  1. customoverall yield as a foam

Sources & evidence

ORD record
ord-ead95ad574264ebf9485172ad6f27770
Source dataset
uspto-grants-1997_05
Patent number
US05627196

Reaction notes

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