1-Butanol → HCID 18378948, compound

HRID 2298882Notes

Reaction equation

HRID 2298882 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[C:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][NH2:19])[CH2:11][C:10]=3[O:20][C:5]=2[CH:4]=1.[Cl:21][C:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[S:24][N:23]=1.C([O-])(O)=O.[Na+].C(O)CCC>C(Cl)Cl>[OH2:2].[ClH:21].[S:24]1[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:22]([NH:19][CH2:18][CH2:17][CH2:16][CH2:15][N:12]2[CH2:13][CH2:14][C:9]3[C:6]4[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=4[O:20][C:10]=3[CH2:11]2)=[N:23]1

Participants

6

Reactant 4

HCID 2631-ButanolHCID 516892Sodium BicarbonateHCID 5981903-Chloro-1,2-benzisothiazoleHCID 18378946HCID 18378946, compound

Product 1

HCID 18378948HCID 18378948, compoundYield 125.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3,4-dihydro-7-methoxybenzofuro[2,3-c]pyridine-2(1H)-butanamine (0.0055 mol), 3-chloro-1,2-benzisothiazole (0.0089 mol) and NaHCO3 (0.01 mol) was stirred for 1.5 hour at 120° C. (melt). 1-Butanol (0.5 ml) was added. The reaction mixture was cooled, then dissolved in CH2Cl2 and purified by column chromatography over silica gel (eluent: CH2Cl2/(CH3OH/NH3) 98/2). The desired fractions were collected and the solvent was evaporated. The residue was dissolved in 2-propanone and converted into the hydrochloric acid salt (1:2) with HCl/2-propanol. The mixture was stirred at room temperature. The precipitate was filtered off and dried, yielding 1.60 g of N-(1,2-benzisothiazol-3-yl)-3,4-dihydro-7-methoxybenzofuro[2,3-c]pyridine-2(1H)-butanamine monohydrochloride monohydrate (61%) (compound 55).

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompurified by column chromatography over silica gel (eluent: CH2Cl2/(CH3OH/NH3) 98/2)
  3. customThe desired fractions were collected
  4. customthe solvent was evaporated
  5. dissolutionThe residue was dissolved in 2-propanone
  6. stirringThe mixture was stirred at room temperature
  7. filtrationThe precipitate was filtered off
  8. customdried

Sources & evidence

ORD record
ord-f44d742ea6364e92b9d6f15a652a66f8
Source dataset
uspto-grants-2002_12
Patent number
US06495555B1

Reaction notes

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