Dichloromethane → HCID 19081832, compound

HRID 963371Notes

Reaction equation

HRID 963371 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9](=[O:25])[CH2:10][CH2:11][CH:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH2:14][CH2:13]2)=[C:4]([O:26]C)[CH:3]=1.B(Br)(Br)Br.C(Cl)Cl.[OH-].[NH4+]>ClC(Cl)C>[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9](=[O:25])[CH2:10][CH2:11][CH:12]2[CH2:13][CH2:14][N:15]([CH2:18][CH2:19][NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH2:16][CH2:17]2)=[C:4]([OH:26])[CH:3]=1

Participants

6

Reactant 4

HCID 6344Dichloromethane3×HCID 14923Ammonium HydroxideHCID 25134Boron tribromideHCID 133076HCID 133076, compound

Product 1

HCID 19081832HCID 19081832, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

1-[4-Amino-5-chloro-2-methoxyphenyl]-3-{1-[2-(methylsulfonyl) aminoethyl]-piperidin-4-yl}propan-1-one (1.19 g, 2.8 mmol), prepared as in Example 11, was dissolved in dichloroethane (50 mL). Boron tribromide in methylene chloride (4 mL, 1.0 g, 4.0 mmol) was added and the mixture was stirred for approximately 12 hours. The mixture was then poured over ice and methylene chloride (150 mL) and ammonium hydroxide) were added. This bilayer mixture was stirred until a solution had formed in the methylene chloride layer. The aqueous layer was removed and combined with fresh methylene chloride (100 mL) and this bilayer mixture was stirred. The methylene chloride layers were combined and dried over potassium carbonate. Filtration and concentration gave 1-(4-amino-5-chloro-2-hydroxyphenyl)-3-{1-[2-(methylsulfonyl)aminoethyl]piperidin-4-yl}propan-1-one (0.8 g, 2.0 -mmol)

Workup

  1. additionwere added
  2. stirringThis bilayer mixture was stirred until a solution
  3. customThe aqueous layer was removed
  4. stirringthis bilayer mixture was stirred
  5. dry with materialdried over potassium carbonate
  6. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-64aa6ffacd704e55aa984c97cd27d9ef
Source dataset
uspto-grants-1998_06
Patent number
US05763458

Reaction notes

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