Diisopropylamine → HCID 23294431, compound

HRID 1955243Notes

Reaction equation

HRID 1955243 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([O:19][CH2:20][C:21]([N:23]1[CH2:28][CH2:27][CH:26]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:25][CH2:24]1)=O)[CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(NC(C)C)(C)C>O1CCCC1>[CH2:29]([CH:26]1[CH2:25][CH2:24][N:23]([CH2:21][CH2:20][O:19][C:14]2[CH:13]=[CH:12][C:11]3[C:16](=[CH:17][CH:18]=[C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH:10]=3)[CH:15]=2)[CH2:28][CH2:27]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 7912DiisopropylamineHCID 23294308HCID 23294308, compound

Product 1

HCID 23294431HCID 23294431, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2-(6-benzyloxy-naphthalen-2-yloxy)-1-(4-benzyl-piperidin-1-yl)-ethanone (0.71 g, 1.53 mmol) in anhydrous tetrahydofuran (25 ml) was added BH3 ·SMe2 (0.62 ml, 6.20 mmol) and diisopropyl amine (0.214 ml, 1.53 mmol), and the solution was refluxed for 18 h under N2. The reaction was cooled in an ice bath and quenched with dropwise addition of methanol (15 ml). The solvent was evaporated, the solid washed with hexanes and evaporated. The solid was washed with hexanes, filtered, and air dried to give 0.69 g (100%) of 4-benzyl-1-[2-(6-benzyloxy-naphthalen-2-yloxy)-ethyl]-piperidine. 1H NMR (CDCl3) 7.64-7.56 (2H, m), 7.45 (2H, d, J=7.3), 7.39-7.003 (12H, m), 5.12 (2H, d, J=3.6), 4.55 (1H, t, J=5.4), 4.51 (1H, t, J=5.4), 3.62 (1H, t, J=5.4), 3.18-3.14 (3H, m), 2.92 (1H, m), 2.60-2.54 (3H, m), 2.15-2.0 (1H, m), 1.66-1.51 (4H, m).

Workup

  1. temperaturethe solution was refluxed for 18 h under N2
  2. temperatureThe reaction was cooled in an ice bath
  3. customquenched with dropwise addition of methanol (15 ml)
  4. customThe solvent was evaporated
  5. washthe solid washed with hexanes
  6. customevaporated
  7. washThe solid was washed with hexanes
  8. filtrationfiltered
  9. customair dried

Sources & evidence

ORD record
ord-02d534f4f6534565b458ba07f98593aa
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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