Water → HCID 20344037, compound

HRID 2049678Notes

Reaction equation

HRID 2049678 reaction equation
[O:1]=[C:2]1[C:12]2([CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][C:4]2[CH:18]=[CH:19][CH:20]=[CH:21][C:3]1=2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[OH:1][CH:2]1[C:12]2([CH2:13][CH2:14][NH:15][CH2:16][CH2:17]2)[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][C:4]2[CH:18]=[CH:19][CH:20]=[CH:21][C:3]1=2

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 20344062HCID 20344062, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20344037HCID 20344037, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2.4 g of 10,11-dihydro-11-oxospiro[dibenz(b,f)thiepin-10,4'-piperidine], free base of Example 3, in 20 ml of tetrahydrofuran is added dropwise to a refluxing slurry of 1.5 g of lithium aluminum hydride in 20 ml of tetrahydrofuran. After total addition, stirring is continued at reflux for an addition 4 hours and then at ambient temperature for 16 hours. Thereafter, the reaction mixture is decomposed by adding sequentially 1.7 ml of water with 1.7 ml of 15% sodium hydroxide and 5.2 ml of water. The diluted mixture is filtered and the filtrate is concentrated under vacuum, providing 10,11-dihydro-11-hydroxyspiro[dibenz(b,f)thiepin-10,4'-piperidine].

Workup

  1. additionAfter total addition
  2. temperatureat reflux for an addition 4 hours
  3. filtrationThe diluted mixture is filtered
  4. concentrationthe filtrate is concentrated under vacuum

Sources & evidence

ORD record
ord-9e3ce6ee9dc843029edeed731712c6e0
Source dataset
uspto-grants-1980_04
Patent number
US04198420

Reaction notes

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