Hydrochloric Acid → Salmeterol

HRID 1936219Notes

Reaction equation

HRID 1936219 reaction equation
CC1(C)[O:7][CH2:6][C:5]2[CH:8]=[C:9]([CH:12]([OH:32])[CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:10]=[CH:11][C:4]=2[O:3]1.Cl>O.CO>[OH:7][CH2:6][C:5]1[CH:8]=[C:9]([CH:12]([OH:32])[CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:10]=[CH:11][C:4]=1[OH:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 101827471-(2,2-dimethyl-4H-benzo[d][1,3]dioxin-6-yl)-2-(6-(4-phenylbutoxy)hexylamino)ethanol

Product 1

HCID 5152SalmeterolYield 43.9%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of 0.6 g (1.32 mmol) [2-(2,2-dimethyl-4H-benzo[1,3]dioxin-6-yl)-2-hydroxyethyl]-6-[4-phenylbutoxy)hexylamine in 20 ml of a 1:1 H2O/MeOH mixture is added 0.15 ml (1.75 mmol) 35% HCl. After allowing the reaction to stir for 48 hr at room temperature, the MeOH is evaporated off at reduced pressure. The resulting aqueous mixture is extracted with 20 ml CH2Cl2. The organic phase is washed sequentially with 20 ml of a saturated NaHCO3 solution and further 20 ml H2O, dried on anhydrous Na2SO4 and evaporated to dryness to yield 0.24 g (43.9%) 2-hydroxymethyl-4-{1-hydroxy-2-[6-(4-phenylbutoxy)hexylamino]ethyl}phenol.

Workup

  1. customthe reaction
  2. customthe MeOH is evaporated off at reduced pressure
  3. extractionThe resulting aqueous mixture is extracted with 20 ml CH2Cl2
  4. washThe organic phase is washed sequentially with 20 ml of a saturated NaHCO3 solution and further 20 ml H2O
  5. dry with materialdried on anhydrous Na2SO4
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-572e128e9e484081a5dc01f09c3e2226
Source dataset
uspto-grants-2002_05
Patent number
US06388134B1

Reaction notes

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