Hydrogen Bromide → HCID 131712691, compound

HRID 2198948Notes

Reaction equation

HRID 2198948 reaction equation
[CH3:1][N:2]([CH3:18])[CH2:3][CH2:4][CH2:5][C:6]1([CH3:17])[CH2:11][CH2:10][C:9]2[CH:12]=[CH:13][CH:14]=[C:15]([OH:16])[C:8]=2[O:7]1.[BrH:19]>CO>[BrH:19].[CH3:18][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][C:6]1([CH3:17])[CH2:11][CH2:10][C:9]2[CH:12]=[CH:13][CH:14]=[C:15]([OH:16])[C:8]=2[O:7]1

Participants

4

Reactant 2

HCID 260Hydrogen Bromide2×HCID 13324380HCID 13324380, compound

Product 1

HCID 131712691HCID 131712691, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4 g of recrystallized 2-[3-(dimethylamino)propyl]-3,4-dihydro-2-methyl-2H-1-benzopyran-8-ol, acetate ester, hydrobromide (1:1), the product of Example 8, (0.012 moles) in 100 ml of methanol is treated with 1 ml of 48% HBr and refluxed for 1 hour. The solvent is evaporated and the resulting oil dissolved in 50 ml of acetonitrile and 50 ml of ethyl acetate. This is treated with DARCO (Trademark) then diluted to 250 ml with ether to give an off-white solid. Recrystallization in the same manner gives 1.7 g (47%) of 2-[3-(dimethylamino)propyl]-3,4-dihydro-2-methyl-2H-1-benzopyran-8-ol, hydrobromide (1:1), mp 132°-135° C.

Workup

  1. temperaturerefluxed for 1 hour
  2. customThe solvent is evaporated
  3. dissolutionthe resulting oil dissolved in 50 ml of acetonitrile
  4. additionThis is treated with DARCO (Trademark)
  5. additionthen diluted to 250 ml with ether
  6. customto give an off-white solid
  7. customRecrystallization in the same manner

Sources & evidence

ORD record
ord-ee8d62e6cefc41bd81c2287771a83604
Source dataset
uspto-grants-1982_11
Patent number
US04360532

Reaction notes

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