Water → HCID 18783154, compound

HRID 1420879Notes

Reaction equation

HRID 1420879 reaction equation
Cl.[CH3:2][C:3]1([NH2:13])[CH2:8][C:7]([CH3:10])([CH3:9])[CH2:6][C:5]([CH3:12])([CH3:11])[CH2:4]1.Br[CH2:15][CH2:16][CH2:17][C:18]#[N:19].C(=O)([O-])[O-].[Na+].[Na+].O>O1CCCC1>[C:18]([CH2:17][CH2:16][CH2:15][NH:13][C:3]1([CH3:2])[CH2:8][C:7]([CH3:10])([CH3:9])[CH2:6][C:5]([CH3:12])([CH3:11])[CH2:4]1)#[N:19]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 214124-BromobutyronitrileHCID 9859105209185-99-9

Product 1

HCID 18783154HCID 18783154, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1,3,3,5,5-pentamethylcyclohexylamine hydrochloride (1) (2-06 g, 10 mmol) 4-bromobutyronitrile (1.55 g. 10.5 mmol) and sodium carbonate (3.18 g, 30 mmol) in tetrahydrofuran (50 ml) was refluxed for 85 h, the poured into water (100 ml) and extracted with ether (3*30 ml). The combined organic phases were washed with brine (20 ml) and dried over K2CO3. The solution was filtered and evaporated and the crude product was purified by chromatography on silica gel, eluting with hexane-ether (10:1), (6:1), (4:1) to give product 2 (1.86 g, 86%) as an colorless oil.

Workup

  1. temperaturewas refluxed for 85 h
  2. extractionextracted with ether (3*30 ml)
  3. washThe combined organic phases were washed with brine (20 ml)
  4. dry with materialdried over K2CO3
  5. filtrationThe solution was filtered
  6. customevaporated
  7. customthe crude product was purified by chromatography on silica gel
  8. washeluting with hexane-ether (10:1), (6:1), (4:1)

Sources & evidence

ORD record
ord-a796cfcc63e2414485e2d642bfbfeadf
Source dataset
uspto-grants-2000_06
Patent number
US06071966

Reaction notes

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