N-Methyl dicyclohexylamine → HCID 57551724, compound

HRID 907327Notes

Reaction equation

HRID 907327 reaction equation
[CH2:1]([N:8]1[CH:17]=[C:16](Br)[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:19]3[CH:20]=[C:21]([CH:26]=[CH:27][C:28]=3[CH3:29])[C:22]([O:24][CH3:25])=[O:23])[CH:14]=2)[C:9]1=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:31][N:32]([CH:39]1CCCCC1)[CH:33]1CCC[CH2:35][CH2:34]1>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C(=O)C>[CH2:1]([N:8]1[CH:17]=[C:16]([CH2:35][CH2:34][CH2:33][N:32]([CH3:39])[CH3:31])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:19]3[CH:20]=[C:21]([CH:26]=[CH:27][C:28]=3[CH3:29])[C:22]([O:24][CH3:25])=[O:23])[CH:14]=2)[C:9]1=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24210N-Methyl dicyclohexylamineHCID 57551818HCID 57551818, compound

Product 1

HCID 57551724HCID 57551724, compound

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of the product from step i) (170 mg), tetrabutylammonium chloride (10 mg), Pd-118 (24 mg) and N-methyldicyclohexylamine (0.12 mL) in N,N-dimethylacetamide (3 mL) was evacuated and flushed with nitrogen (×3) before the addition of allyl alcohol (0.05 mL). The resultant solution was stirred under nitrogen at 70° C. for 2 hours. The reaction mixture was cooled to room temperature and dilute hydrochloric acid (1N, 2 mL) was added, followed by dichloromethane (10 mL). The resulting suspension was filtered and the filtrate was washed with water (2×5 mL). The organic phase was separated and treated with dimethylamine hydrochloride (0.181 g) followed by sodium triacetoxyborohydride (0.157 g). The mixture was then stirred at room temperature for 30 minutes. The reaction mixture was filtered and poured directly onto a silica column (10 g) (eluting with 3% methanol in dichloromethane) to afford the sub-titled compound (0.12 g).

Workup

  1. customwas evacuated
  2. customflushed with nitrogen (×3) before the addition of allyl alcohol (0.05 mL)
  3. temperatureThe reaction mixture was cooled to room temperature
  4. additiondilute hydrochloric acid (1N, 2 mL) was added
  5. filtrationThe resulting suspension was filtered
  6. washthe filtrate was washed with water (2×5 mL)
  7. customThe organic phase was separated
  8. additiontreated with dimethylamine hydrochloride (0.181 g)
  9. stirringThe mixture was then stirred at room temperature for 30 minutes
  10. filtrationThe reaction mixture was filtered
  11. additionpoured directly onto a silica column (10 g) (eluting with 3% methanol in dichloromethane)

Sources & evidence

ORD record
ord-f6c5f613139748fb888ffef9a26add68
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

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