Water → HCID 9912262, compound

HRID 430711Notes

Reaction equation

HRID 430711 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:34])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][C:17]3(C#N)[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[CH2:21][S:20][C:19]4[CH:28]=[CH:29][CH:30]=[CH:31][C:18]3=4)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.O.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([OH:34])[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][CH2:16][CH:17]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[CH2:21][S:20][C:19]4[CH:28]=[CH:29][CH:30]=[CH:31][C:18]3=4)[CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 14798Sodium HydroxideHCID 5311125HCID 5311125, compound

Product 1

HCID 9912262HCID 9912262, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4-chlorophenyl)-1-[3-(11-cyano-6,11- dihydrodibenzo[b,e]thiepin-11-yl)propyl]piperidin-4-ol (430mg) in THF 10ml) was added 1M lithium aluminum hydride THF solution (1.5 ml) and the mixture was heated to reflux for 3 hours. The reaction mixture was cooled with ice, water (0.06 ml), then 15% aqueous sodium hydroxide (0.06 ml), then water (0.18 ml) were added carefully. The granular salt was filtered off and the filtrate was distilled off under reduced pressure. The residue was purified by silica gel chromatography eluting with ethyl acetate-hexane (1:1) to give the titled compound (280mg). 1H-NMR (CDCl3) d: 1.55-1.80(4H,m), 2.03-2.16(2H,m), 2.25-2.52(6H,m), 2.72-2.80(2H,m), 3.90(1H,brs), 4.48(1H,brt), 4.68(1H,brs), 6.96-7.45(12H,m). MS m/z: 464(M+1)

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 hours
  3. filtrationThe granular salt was filtered off
  4. distillationthe filtrate was distilled off under reduced pressure
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with ethyl acetate-hexane (1:1)

Sources & evidence

ORD record
ord-fdb86865bff84326a40437d02874d3f6
Source dataset
uspto-grants-2001_11
Patent number
US06323206B1

Reaction notes

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