Hydrochloric Acid → HCID 10345357, compound

HRID 2223674Notes

Reaction equation

HRID 2223674 reaction equation
Cl.C[O:3][C:4]1[CH:5]=[CH:6][C:7]2[C:11]([C:12]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][N:23]4[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]4)=[CH:16][CH:15]=3)=[O:13])=[C:10]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[O:36]C)[S:9][C:8]=2[CH:38]=1.Cl.CCOCC>C(Cl)Cl.CC(O)C.C(Cl)(Cl)Cl>[OH:3][C:4]1[CH:5]=[CH:6][C:7]2[C:11]([C:12]([C:14]3[CH:15]=[CH:16][C:17]([O:20][CH2:21][CH2:22][N:23]4[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]4)=[CH:18][CH:19]=3)=[O:13])=[C:10]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[OH:36])[S:9][C:8]=2[CH:38]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10953452Ether hydrochlorideHCID 22046617HCID 22046617, compound

Product 1

HCID 10345357HCID 10345357, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21906603Chloroform isopropyl alcoholSolvent

Conditions

Temperature
0 °C

Procedure

Prepare the HCl salt of [6-methoxy-2-(2-methoxy-benzyl)-benzo[b]thiophen-3-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone by adding sat. HCl/Ether to a solution in CH2Cl2. Concentrate to dryness and redissolve in CH2Cl2 (5 mL). Cool this solution to 0° C. and add BBr3 (1 mL). Stir for 2 h while warming to r.t. Quench the reaction with sat. NaHCO3 and dilute with i-PrOH/CHCl3 (1:3). Wash the organic phase with water and brine, dry over MgSO4, filter and concentrate. Purify the crude by flash chromatography (0-5% (2M NH3 in MeOH)/CH2Cl2) to afford [6-hydroxy-2-(2-hydroxy-benzyl)-benzo[b]thiophen-3-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (300 mg, 54%, 2 steps).

Workup

  1. concentrationConcentrate to dryness
  2. dissolutionredissolve in CH2Cl2 (5 mL)
  3. additionadd BBr3 (1 mL)
  4. temperaturewhile warming to r.t
  5. customQuench
  6. customthe reaction with sat. NaHCO3
  7. washWash the organic phase with water and brine
  8. dry with materialdry over MgSO4
  9. filtrationfilter
  10. concentrationconcentrate
  11. customPurify the crude by flash chromatography (0-5% (2M NH3 in MeOH)/CH2Cl2)

Sources & evidence

ORD record
ord-80ffc370291f4ed2832fd61287adf661
Source dataset
uspto-grants-2008_05
Patent number
US07375229B2

Reaction notes

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