Sodium Hydroxide → 1-{benzyl[2-(2-methoxyphenoxy)ethyl]amino}-3-(9H-carbazol-4-yloxy)propan-2-ol

HRID 1836716Notes

Reaction equation

HRID 1836716 reaction equation
C1(S([N:10]2[C:22]3[CH:21]=[CH:20][CH:19]=[C:18]([O:23][CH2:24][CH:25]([OH:46])[CH2:26][N:27]([CH2:39][C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[CH2:28][CH2:29][O:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=4[O:37][CH3:38])[C:17]=3[C:16]3[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=3)(=O)=O)C=CC=CC=1.[OH-].[Na+]>C1COCC1.CO.O>[CH2:39]([N:27]([CH2:28][CH2:29][O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[O:37][CH3:38])[CH2:26][CH:25]([OH:46])[CH2:24][O:23][C:18]1[C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:22]=2[CH:21]=[CH:20][CH:19]=1)[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 114792061-(9-Benzenesulfonyl-9H-carbazol-4-yloxy)-3-{benzyl-[2-(2-methoxy-phenoxy)-ethyl]-amino}-propan-2-ol

Product 1

HCID 110383641-{benzyl[2-(2-methoxyphenoxy)ethyl]amino}-3-(9H-carbazol-4-yloxy)propan-2-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

3.3 g of 1-(9-Benzenesulfonyl-9H-carbazol-4-yloxy)-3-{benzyl-[2-(2-methoxyphenoxy)-ethyl]-amino}-propan-2-ol (5.2 mmol) were dissolved in 33 ml THF/methanol (2:1). A solution of 1.1 g of sodium hydroxide in 1.7 ml of water was added in one portion. The mixture was stirred for 18 h at 50° C. The mixture was rotary evaporated (35° C./20 mbar). The residue was dissolved in 25 ml of toluene and 20 ml of water. The phases were separated and the toluene phase was washed 3 times with 25 ml of water. The organic phase was rotary evaporated (40° C./15 mbar) and the residue was crystallized with 9 ml ethanol. The product was filtered under suction and washed twice with 3 ml cold ethanol. The substance was dried at 50° C. for 12 h.

Workup

  1. customThe mixture was rotary evaporated (35° C./20 mbar)
  2. dissolutionThe residue was dissolved in 25 ml of toluene
  3. customThe phases were separated
  4. washthe toluene phase was washed 3 times with 25 ml of water
  5. customThe organic phase was rotary evaporated (40° C./15 mbar)
  6. customthe residue was crystallized with 9 ml ethanol
  7. filtrationThe product was filtered under suction
  8. washwashed twice with 3 ml cold ethanol
  9. customThe substance was dried at 50° C. for 12 h.

Sources & evidence

ORD record
ord-66a1b68301bd4820b27d646059d45416
Source dataset
uspto-grants-2004_08
Patent number
US06777559B2

Reaction notes

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