4-Piperidinol, 1-(1H-indol-3-yloxoacetyl)-4-phenyl- → HCID 12589402, compound

HRID 1576485Notes

Reaction equation

HRID 1576485 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[CH2:18][CH2:17][C:16]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)([OH:19])[CH2:15][CH2:14]2)=O)=[CH:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:19][C:16]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:15][CH2:14][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)[CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 2055944-Piperidinol, 1-(1H-indol-3-yloxoacetyl)-4-phenyl-HCID 21226445Aluminium lithium hydride

Product 1

HCID 12589402HCID 12589402, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 17.0 g. (0.049 mole) of 1-(indol-3-ylglyoxyloyl)-4-phenyl-4-piperidinol in 100 ml. of tetrahydrofuran was reduced in the usual way with 7.4 g. (0.195 mole) of lithium aluminum hydride in 200 ml. of tetrahydrofuran. After the usual workup 11.6 g. of oil was obtained which was crystallized from benzene-isooctane yielding 8.6 g. (55%) of product which melted at 133°-137° C. Another recrystallization from benzene raised the melting point to 137°-139° C. The analytical sample melted at 137°-139° C.

Workup

  1. customof oil was obtained which
  2. customwas crystallized from benzene-isooctane yielding 8.6 g
  3. customAnother recrystallization from benzene
  4. temperatureraised the melting point to 137°-139° C

Sources & evidence

ORD record
ord-8a2e53330eaf4964a3f569b999ddd63b
Source dataset
uspto-grants-1976_09
Patent number
USRE028973

Reaction notes

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