Water → HCID 9882968, compound

HRID 2395268Notes

Reaction equation

HRID 2395268 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl.[CH2:8]([N:15]1[CH2:20][CH2:19][N:18]([C:21]([C:23]2[NH:24][C:25]3[C:30]([CH:31]=2)=[CH:29][CH:28]=[CH:27][CH:26]=3)=O)[CH2:17][CH2:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O.[OH-].[Na+]>C1COCC1>[CH2:8]([N:15]1[CH2:16][CH2:17][N:18]([CH2:21][C:23]2[NH:24][C:25]3[C:30]([CH:31]=2)=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:19][CH2:20]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 18971629HCID 18971629, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 9882968HCID 9882968, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminium hydride in THF (1M, 11.25 mmol) was slowly added to a suspension of 2-(4-benzylpiperazin-1-yl)carbonyl indole hydrochloride (2.0 g, 5.6 mmol) in THF (40 ml) under a nitrogen atmosphere and the resultant solution heated at reflux for 90 min. The mixture was cooled to room temperature and treated sequentially with water (0.5 ml), sodium hydroxide (4M, 0.5 ml) and water (1.5 ml). The mixture was filtered and the filtrate evaporated in vacuo. The residue was recrystallised from toluene to afford the title compound as a white solid (428 mg, 25%), m.p. 157°-159° C.; (Found: C, 78.44; H, 7.63; N, 13.66. C20 H23N3 requires C, 78.65; H, 7.59; N, 13.76%); δH (DMSO-d6) 2.40 (8H, br s, 4×piperazinyl CH2), 3.45 (2H, s, CH2), 3.59 (2H, s, CH2), 6.23 (1H, s, 3-H), 6.90 (1H, m, ArH), 6.95 (1H, m, ArH), 7.20-7.32 (6H, m, ArH), 7.42 (1H, d, J 7.7 Hz, ArH), and 10.93 (1H, br s, NH); m/z (CI+, NH3) 306 (M+1)+.

Workup

  1. temperatureat reflux for 90 min
  2. filtrationThe mixture was filtered
  3. customthe filtrate evaporated in vacuo
  4. customThe residue was recrystallised from toluene

Sources & evidence

ORD record
ord-5420824f0abf4cdba910b2652252bac6
Source dataset
uspto-grants-1998_09
Patent number
US05814644

Reaction notes

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