Trifluoroacetic acid → N,N-diethyl-4-(bromo-N-benzyl-piperidin-4-ylidene-methyl)-benzamide

HRID 1791342Notes

Reaction equation

HRID 1791342 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][C:11](=[C:14]([Br:28])[C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:27])[N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C(Br)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(N(CC)CC)C>ClCCl>[CH2:25]([N:22]([CH2:23][CH3:24])[C:21](=[O:27])[C:18]1[CH:17]=[CH:16][C:15]([C:14]([Br:28])=[C:11]2[CH2:12][CH2:13][N:8]([CH2:6][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH2:9][CH2:10]2)=[CH:20][CH:19]=1)[CH3:26]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7498Benzyl BromideHCID 8471TriethylamineHCID 10503756HCID 10503756, compound

Product 1

HCID 11374090N,N-diethyl-4-(bromo-N-benzyl-piperidin-4-ylidene-methyl)-benzamideYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Compound 6, prepared in Example 1 (v) above (6.122 g, 13.4 mmoL), was treated with TFA (13 mL) in dichloromethane (80 mL) at room temperature. After 2 h, the reaction mixture was washed with 2M sodium hydroxide (25 mL) and the organic layer was separated. The organic layer was dried (MgSO), filtered and concentrated. The residue was dissolved in dichloromethane (120 mL), cooled to 0° C. and benzyl bromide (1.8 mL, 15.1 mmol) and triethylamine (5.7 mL, 41.0 mmol) were added. The reaction was gradually warmed to room temperature and after 20 hours the reaction was washed with water (1×100 mL). The organic layer was dried (MgSO4), filtered and concentrated. Purification by flash chromatography, eluting 50 to 60% ethyl acetate in hexanes gave 3.80 g of product (64% yield).

Workup

  1. washthe reaction mixture was washed with 2M sodium hydroxide (25 mL)
  2. customthe organic layer was separated
  3. dry with materialThe organic layer was dried (MgSO)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in dichloromethane (120 mL)
  7. temperatureThe reaction was gradually warmed to room temperature and after 20 hours the reaction
  8. washwas washed with water (1×100 mL)
  9. dry with materialThe organic layer was dried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customPurification by flash chromatography
  13. washeluting 50 to 60% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-701b5f1c918649d0a0cd6ae9ff8a1478
Source dataset
uspto-grants-2006_07
Patent number
US07074808B2

Reaction notes

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