1-Butanaminium, N,N,N-tributyl-, fluoride, hydrate → HCID 58815850, compound

HRID 2245890Notes

Reaction equation

HRID 2245890 reaction equation
O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:20]([N:22]([CH2:54][CH2:55][O:56][Si](CC)(CC)CC)[C:23](=[O:53])[C:24]1[CH:29]=[CH:28][C:27]([C@@H:30]([N:37]2[CH2:42][C@@H:41]([CH3:43])[N:40]([CH2:44][C:45]3[CH:50]=[CH:49][CH:48]=[C:47]([F:51])[CH:46]=3)[CH2:39][C@@H:38]2[CH3:52])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:26][CH:25]=1)[CH3:21]>C1COCC1>[CH2:20]([N:22]([CH2:54][CH2:55][OH:56])[C:23](=[O:53])[C:24]1[CH:29]=[CH:28][C:27]([C@@H:30]([N:37]2[CH2:42][C@@H:41]([CH3:43])[N:40]([CH2:44][C:45]3[CH:50]=[CH:49][CH:48]=[C:47]([F:51])[CH:46]=3)[CH2:39][C@@H:38]2[CH3:52])[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[CH:26][CH:25]=1)[CH3:21]

Participants

4

Reactant 2

HCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrateHCID 58815954HCID 58815954, compound

Product 1

HCID 58815850HCID 58815850, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride hydrate (1.83 g) was added to the solution of N-Ethyl-4-{(S)-[(2S,5R)-4-(3-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-phenyl-methyl}-N-(2-triethylsilanyloxy-ethyl)-benzamide (3.6 g) in THF (30 mL). The reaction was stirred at room temperature for 90 minutes. The reaction mixture was concentrated. The residual was dissolved in EtOAc (60 mL). The EtOAc solution was washed by H2O (30 mL×3) and brine (30 mL×1), dried by Na2SO4 and concentrated to give crude product (3.3 g), which was purified to give pure N-Ethyl-4-{(S)-[(2S,5R)-4-(3-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-phenyl-methyl}-N-(2-hydroxy-ethyl)-benzamide (2.76 g; 94%). 1H NMR (300 MHz, CDCl3) □ 7.49 (m, 2H), 7.37-7.19 (m, 8H), 7.04 (m, 2H), 6.90 (ddd, 1H, J=8.5, 8.5, 2.0 Hz), 5.16 (s, 1H), 3.87 (m, 3H), 3.69 (m, 2H), 3.36 (m, 2H), 3.18 (d, 1H, J=13.5 Hz), 2.67 (m, 2H), 2.56 (m, 2H), 1.97 (m, 2H), 1.67 (s, 1H), 1.16 (m, 3H), 1.12 (d, 3H, J=6.0 Hz), 1.06 (d, 3H, J=6.5 Hz).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionThe residual was dissolved in EtOAc (60 mL)
  3. washThe EtOAc solution was washed by H2O (30 mL×3) and brine (30 mL×1)
  4. dry with materialdried by Na2SO4
  5. concentrationconcentrated
  6. customto give crude product (3.3 g), which
  7. customwas purified

Sources & evidence

ORD record
ord-853c1afed62842aca8b1b97e850f0cb8
Source dataset
uspto-grants-2010_03
Patent number
US07683168B2

Reaction notes

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