Oxalic Acid → HCID 131719708, compound

HRID 1900965Notes

Reaction equation

HRID 1900965 reaction equation
[O:1]1[CH2:3][CH:2]1[CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2.[C:15]1([CH2:21][CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:28]([OH:33])(=[O:32])[C:29]([OH:31])=[O:30]>C(OCC)(=O)C>[C:28]([OH:33])(=[O:32])[C:29]([OH:31])=[O:30].[NH:10]1[C:11]2[C:7](=[C:6]([O:5][CH2:4][CH:2]([OH:1])[CH2:3][N:25]3[CH2:26][CH2:27][CH:22]([CH2:21][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH2:23][CH2:24]3)[CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:9]1

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 317384-BenzylpiperidineHCID 6050154-(oxiran-2-ylmethoxy)-1H-indole

Product 1

HCID 131719708HCID 131719708, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

The title compound was prepared in similar fashion from 4-(oxiranylmethoxy)-1H-indole and 4-phenylmethylpiperidine. The resulting free base was dissolved in ethyl acetate, and precipitated with one equivalent of oxalic acid in ethyl acetate in 52% overall yield. FDMS m/e=364 (M+ of free base). mp 105°-107°.

Sources & evidence

ORD record
ord-b72ab1c17275427a84ccc87c8a7ce591
Source dataset
uspto-grants-1996_11
Patent number
US05576321

Reaction notes

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