Oxalic Acid → HCID 131719714, compound

HRID 1900998Notes

Reaction equation

HRID 1900998 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.[CH:15]1([CH2:18][O:19][C:20]2[CH:28]=[CH:27][CH:26]=[C:25]3[C:21]=2[C:22]([C:29]2[CH2:30][CH2:31][NH:32][CH2:33][CH:34]=2)=[CH:23][NH:24]3)[CH2:17][CH2:16]1.[C:35]([OH:40])(=[O:39])[C:36]([OH:38])=[O:37]>C(OCC)(=O)C>[C:35]([OH:40])(=[O:39])[C:36]([OH:38])=[O:37].[NH:10]1[C:11]2[C:7](=[C:6]([O:5][CH2:4][CH2:3][CH2:2][N:32]3[CH2:33][CH:34]=[C:29]([C:22]4[C:21]5[C:25](=[CH:26][CH:27]=[CH:28][C:20]=5[O:19][CH2:18][CH:15]5[CH2:16][CH2:17]5)[NH:24][CH:23]=4)[CH2:30][CH2:31]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 21268233HCID 21268233, compound

Product 1

HCID 131719714HCID 131719714, 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-(4-cyclopropylmethoxy-1H-indol-3-yl)-1,2,3,6-tetrahydropyridine (which was prepared by condensing 4-cyclopropylmethoxyindole with 4-piperidone monohydrate hydrochloride in refluxing methanol with potassium hydroxide). The resulting free base was dissolved in ethyl acetate, and precipitated with one equivalent of oxalic acid in ethyl acetate in 20% overall yield as a white foam. FDMS m/e=441 (M+ of free base).

Workup

  1. customoverall yield as a white foam

Sources & evidence

ORD record
ord-9164b6c7d4ca45a285d25960d6d338e7
Source dataset
uspto-grants-1996_11
Patent number
US05576321

Reaction notes

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