Oxalic Acid → HCID 131719714, compound

HRID 565530Notes

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.C1([C:18]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:19]=2[C:20]([C:29]2[CH2:30][CH2:31][NH:32][CH2:33][CH:34]=2)=[CH:21][N:22]3OC)CC1.[C:35]([OH:40])(=[O:39])[C:36]([OH:38])=[O:37].C([O:44][CH2:45][CH3:46])(=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:20]4[C:19]5[C:23](=[CH:24][CH:25]=[CH:26][C:18]=5[O:44][CH2:45][CH:46]5[CH2:36][CH2:35]5)[NH:22][CH:21]=4)[CH2:30][CH2:31]3)[CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:9]1

Participants

Reactant 4

HCID 971Oxalic Acid

HCID 8857Ethyl Acetate2×

HCID 116941694-(3-chloropropoxy)-1H-indole

HCID 70217234HCID 70217234, compound

Product 1

HCID 131719714HCID 131719714, compound

Procedure

The title compound was prepared in similar fashion from 1-chloro-3-(1H-indole-4-oxy)propane and 4-(4-cyclopropyl-methoxy-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

customoverall yield as a white foam

Sources & evidence

ORD record: ord-3db12d468fac467eae92c68c27faf9ac
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06172073B2

Reaction notes

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