Hydrochloric Acid → HCID 131710451, compound

HRID 1576483Notes

Reaction equation

HRID 1576483 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10](=O)[C:11]([N:13]2[CH2:17][CH2:16][CH:15]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[O:25][CH3:26])[CH2:14]2)=O)=[CH:2]1.O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[ClH:39]>CCOCC>[ClH:39].[CH3:26][O:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[O:18][CH:15]1[CH2:16][CH2:17][N:13]([CH2:11][CH2:10][C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)[CH2:14]1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 21510717HCID 21510717, compound

Product 1

HCID 131710451HCID 131710451, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 13.5 g. (0.037 mole) of 1 -(indole-3-ylglyoxyloyl)-3-(o-methoxyphenoxy)pyrrolidine in 50 ml. of anhydrous tetrahydrofuran was added dropwise to a stirred slurry of 7 g. (0.18 mole) of lithium aluminum hydride in 150 ml. of anhydrous tetrahydrofuran. The reaction mixture was worked up in the usual manner and the oily basic material which was isolated was dissolved in ether and treated with ethereal hydrogen chloride. The isolated hydrochloride weighed 10.7 g. (73%) and melted with decomposition (gas evolution) near a55° C. as a result of solvated ether. Thin layer chromatography of a sample of regenerated free base showed a single spot.

Workup

  1. customthe oily basic material which was isolated

Sources & evidence

ORD record
ord-e21b9bb7d212485cb6d4dd8046bcbab7
Source dataset
uspto-grants-1976_09
Patent number
USRE028973

Reaction notes

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