HCID 20394272, compound → HCID 20394285, compound

HRID 261504Notes

Reaction equation

HRID 261504 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16](=O)[C:17]([N:19]2[CH2:24][CH2:23][C:22]3([CH2:28][C:27]4[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=4[O:25]3)[CH2:21][CH2:20]2)=O)=[CH:8]1>O1CCCC1>[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH2:16][CH2:17][N:19]2[CH2:24][CH2:23][C:22]3([CH2:28][C:27]4[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=4[O:25]3)[CH2:21][CH2:20]2)=[CH:8]1

Participants

4

Reactant 2

HCID 20394272HCID 20394272, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20394285HCID 20394285, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred suspension under nitrogen of 1.5 g of lithium aluminum hydride in 150 ml of tetrahydrofuran is treated with a solution of 2,3-dihydro-1'-(indol-3-ylglyoxyloyl)spiro[benzofuran-2,4'-piperidine], Example 22, in 75 ml of tetrahydrofuran according to the procedure of Example 22 to provide a tan solid. The solid is successively recrystallized from an ethyl alcohol-water mixture, chromatographed through a silica gel column with a 2% methyl alcohol in chloroform eluant and recrystallized from ethyl alcohol to provide the product, 2,3-dihydro-1'-[2-(3-indolyl)ethyl]spiro[benzofuran-2,4'-piperidine], mp 167°-169° C.

Workup

  1. customto provide a tan solid
  2. customThe solid is successively recrystallized from an ethyl alcohol-water mixture
  3. customchromatographed through a silica gel column with a 2% methyl alcohol in chloroform eluant
  4. customrecrystallized from ethyl alcohol

Sources & evidence

ORD record
ord-f869e94a733d4ee1a1196c54b8c4ba0a
Source dataset
uspto-grants-1979_08
Patent number
US04166119

Reaction notes

Loading…