HCID 86758490, compound → HCID 18434266, compound

HRID 2306489Notes

Reaction equation

HRID 2306489 reaction equation
[CH2:1]([N:4]([CH3:29])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([C:20]2[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][CH:21]=2)=[O:19])=[C:14]([O:27]C)[CH:13]=1)[CH:2]=[CH2:3].[C:30]([O-:37])(=[O:36])/[CH:31]=[CH:32]/[C:33]([O-:35])=[O:34]>C(Cl)Cl>[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34].[CH2:1]([N:4]([CH3:29])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([C:20]2[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][CH:21]=2)=[O:19])=[C:14]([OH:27])[CH:13]=1)[CH:2]=[CH2:3]

Participants

3

Reactant 1

HCID 86758490HCID 86758490, compound

Product 1

HCID 18434266HCID 18434266, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The fumarate obtained is taken up in methylene chloride/saturated sodium bicarbonate solution and the organic phase is dried and concentrated. 3.09 g of the thus-obtained [4-[6-(allyl-methyl-amino)-hexyloxy]-2-methoxy-phenyl]-(4-bromo-phenyl)-methanone are boiled in 13 ml of acetic acid/7.7 ml of 62% HBr solution at 90° C. for 2 hrs. The reaction mixture is concentrated and the residue is converted into the free base with methylene chloride/saturated sodium bicarbonate solution. The residue is treated with 0.74 g of fumaric acid and processed using ethanol/ether. There are obtained 2.05 g of [4-[6-(allyl-methyl-amino)-hexyloxy]-2-hydroxy-phenyl]-(4-bromo-phenyl)-methanone fumarate, MS: m/e 446 (M+H+, 1Br).

Workup

  1. customthe organic phase is dried
  2. concentrationconcentrated
  3. concentrationThe reaction mixture is concentrated
  4. additionThe residue is treated with 0.74 g of fumaric acid

Sources & evidence

ORD record
ord-3b2da40094c44783887f3dc4b1c4c1dd
Source dataset
uspto-grants-2002_08
Patent number
US06441177B1

Reaction notes

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