4-tert-Butylbenzylamine → (4-Tert-butyl-benzyl)-[2-(tetrahydro-thiopyran-4-yl)-ethyl]-amine

HRID 855177

Reaction equation

HRID 855177 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH2:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[S:13]1[CH2:18][CH2:17][CH:16]([CH2:19][CH:20]=O)[CH2:15][CH2:14]1.[BH4-].[Na+]>CO.Cl>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][NH:10][CH2:20][CH2:19][CH:16]2[CH2:17][CH2:18][S:13][CH2:14][CH2:15]2)=[CH:11][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 27356554-tert-ButylbenzylamineHCID 4311764Sodium borohydrideHCID 23532962(Tetrahydro-thiopyran-4-YL)-acetaldehyde

Product 1

HCID 69342005(4-Tert-butyl-benzyl)-[2-(tetrahydro-thiopyran-4-yl)-ethyl]-amineYield 87%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

0.44 ml of 4-tert-butylbenzylamine (2.5 mmol) and 541 mg (tetrahydro-thiopyran-4-yl)-acetaldehyde (3.75 mmol) were dissolved in 7.5 ml methanol and stirred for 30 min at rt and then refluxed for 2.5 h. After cooling down to rt, 114 mg (3 mmol) of sodium borohydride were added and after stirring for 15 min at rt, the reaction mixture was refluxed for 2¾ h. After cooling down to rt, the reaction mixture was treated with 5 drops 1 N HCl and concentrated in vacuo. The residue was diluted with water/EtOAc. After separation of the organic phase, the aqueous phase was extracted with EtOAc and the combined organic phases were washed with brine, dried with magnesium sulfate, filtered off and concentrated in vacuo. The residue was purified by column chromatography (90 g silica gel; EtOAc/heptane 1:2 then EtOAc) to give 632 mg light yellow viscous oil (87%). MS (ISP) 292.3 (M+H)+.

Workup

  1. temperaturerefluxed for 2.5 h
  2. temperatureAfter cooling down to rt
  3. stirringafter stirring for 15 min at rt
  4. temperaturethe reaction mixture was refluxed for 2¾ h
  5. temperatureAfter cooling down to rt
  6. concentrationconcentrated in vacuo
  7. additionThe residue was diluted with water/EtOAc
  8. customAfter separation of the organic phase
  9. extractionthe aqueous phase was extracted with EtOAc
  10. washthe combined organic phases were washed with brine
  11. dry with materialdried with magnesium sulfate
  12. filtrationfiltered off
  13. concentrationconcentrated in vacuo
  14. customThe residue was purified by column chromatography (90 g silica gel

Sources & evidence

ORD record
ord-d72b0d96ae2c430e9a02ed5ef497f832
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Linked notes

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