Hydrogen Bromide → HCID 18621546, compound

HRID 1861766Notes

Reaction equation

HRID 1861766 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][CH2:11][N:10]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22]C(OC(C)(C)C)=O)=[CH:18][CH:17]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BrH:30]>>[BrH:30].[CH2:1]([CH:8]1[CH2:13][CH2:12][CH2:11][N:10]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 18621483HCID 18621483, compound

Product 1

HCID 18621546HCID 18621546, compoundYield 55%

Conditions

Temperature
25 °C

Procedure

3-benzyl-1-[2-(4-tert-butoxycarbonylaminophenyl) ethyl]piperidine (0.67 g, 1.69 mmol) was dissolved in HBr (saturated solution in methanol, 10 mL) and the resulting solution stirred at 25° C. for 20 h. Then, after concentration in vacuum, the resultant mixture was treated with NaHCO3(water saturated solution, 50 mL) and extracted twice with EtOAc (2×50 mL). The collected organic phase was washed with brine (50 mL), dried and concentrated in vacuum. The crude compound was purified by filtration on silica gel using CH2Cl2/MeOH as eluant to afford the free amine as a pale yellow oil (0.272 g, 55%). 1H NMR (CDCl3): 0.85-1.05 (m, 1H), 1.5-1.9 (m, 4H), 1.9-2.1 (m, 2H), 2.4-2.6 (m, 4H), 2.65-2.8 (m, 2H), 2.85-3.05 (m, 2H), 3.53 (bs, 2H), 6.61 (d, J=8.1Hz, 2H), 6.97 (d, J=8.1 Hz, 2H), 7.145 (d, J=7.8Hz, 2H), 7.18 (d, J=7.2, 1H), 7.275 (t, J-7.2Hz, 2H).

Workup

  1. concentrationThen, after concentration in vacuum
  2. additionthe resultant mixture was treated with NaHCO3(water saturated solution, 50 mL)
  3. extractionextracted twice with EtOAc (2×50 mL)
  4. washThe collected organic phase was washed with brine (50 mL)
  5. customdried
  6. concentrationconcentrated in vacuum
  7. filtrationThe crude compound was purified by filtration on silica gel

Sources & evidence

ORD record
ord-33e0a1b2712442629d7d86153a3c11c6
Source dataset
uspto-grants-2003_03
Patent number
US06534522B2

Reaction notes

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