Oxalic Acid → HCID 131719714, compound

HRID 977380Notes

Reaction equation

HRID 977380 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 FDMS m/e=441 (M+ of free base)

Sources & evidence

ORD record
ord-6230bbc10463457baa3cc5467befba6b
Source dataset
uspto-grants-1997_03
Patent number
US05614523

Reaction notes

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