Water → 3,4-Dihydro-1,5-benzothiazepin-5(2h)-amine

HRID 50979Notes

Reaction equation

HRID 50979 reaction equation
[N:1]([N:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[S:7][CH2:6][CH2:5][CH2:4]1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[S:7]1[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:3]([NH2:1])[CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 12233800HCID 12233800, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 122338023,4-Dihydro-1,5-benzothiazepin-5(2h)-amineYield 59.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-nitroso-2,3,4,5-tetrahydro-1,5-benzothiazepine (32.21 g, 0.166 mol) in THF (650 mL) was added dropwise to LAH (1.0M in THF, 166 mL) under N2 such that the temperature did not rise above 27-29° C. Once the addition was complete, the mixture was stirred at room temperature for 1 hr. It was cooled in an ice bath and treated with H2O (7.3 mL) added dropwise, followed by 1N NaOH (32.4 mL). Once at room temperature, the mixture was filtered and the filtrate was evaporated under reduced pressure. The residue was taken up in CH2Cl2 (200 mL) washed with H2O, and dried over MgSO4, and stripped of solvent under reduced pressure to yield 29.42 g (98%) of the crude product. Purification by column chromatography (EtOAc) afforded 17.69 g (59% yield) of 3,4-dihydro-1,5-benzothiazepin-5(2H)-amine as a liquid which was converted to the HCl salt, m.p. 202° C. (decomposition). (M+H)+ 180.

Workup

  1. customdid not rise above 27-29° C
  2. additionOnce the addition
  3. temperatureIt was cooled in an ice bath
  4. additionadded dropwise
  5. filtrationOnce at room temperature, the mixture was filtered
  6. customthe filtrate was evaporated under reduced pressure
  7. washwashed with H2O
  8. dry with materialdried over MgSO4
  9. customto yield 29.42 g (98%) of the crude product
  10. customPurification by column chromatography (EtOAc)

Sources & evidence

ORD record
ord-c28e810b48384baba252a0909a1fc62c
Source dataset
uspto-grants-2004_03
Patent number
US06713471B1

Reaction notes

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