Benzyl Bromide → HCID 54247483, compound

HRID 52259Notes

Reaction equation

HRID 52259 reaction equation
[NH2:1][C@@H:2]1[CH2:7][C:6]2[C:8]([O:13][CH3:14])=[CH:9][CH:10]=[C:11]([Br:12])[C:5]=2[O:4][CH2:3]1.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:12][C:11]1[C:5]2[O:4][CH2:3][C@H:2]([N:1]([CH2:7][C:6]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:5]=3)[CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:7][C:6]=2[C:8]([O:13][CH3:14])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 22871216(3R)-8-bromo-5-methoxychroman-3-amine

Product 1

HCID 54247483HCID 54247483, compoundYield 155.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

(R)-3-Amino-8-bromo-5-methoxy-3,4-dihydro-2H-1-benzopyran (11.5 g, 44 mmol) was dissolved in 400 mL anhydrous acetonitrile and to the reaction were benzyl bromide (13 mL, 110 mmol), anhydrous potassium carbonate (grounded) (16 g, 116 mmol), and a catalytic amount of KI added and then heated to 85° C. for 48 h. The solvent was removed in vacuo, the remains were taken into a 2M solution of NH3 and then extracted twice with ether. The combined ether portions were treated with brine, dried (MgSO4), filtered, and the solvent removed in vacuo to give the crude residue. Chromatography on silica (eluent: CH2Cl2) gave 15 g (78% yield) of the title compound as a clear oil. [α]21D =-15.5° (C=0.1 CHCl3) GC-MS (70eV) M=437 (15%).

Workup

  1. additiona catalytic amount of KI added
  2. customThe solvent was removed in vacuo
  3. extractionextracted twice with ether
  4. additionThe combined ether portions were treated with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customto give the crude residue

Sources & evidence

ORD record
ord-e26526080f754ba2a9e1f28760042046
Source dataset
uspto-grants-1997_04
Patent number
US05616610

Reaction notes

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