Sodium Carbonate → 1,1-dimethylethyl [4-(3,4-dihydro[1]benzothieno[3,2-c]pyridine-2(1H)-yl)butyl]carbamate

HRID 1835691Notes

Reaction equation

HRID 1835691 reaction equation
Cl.[CH2:2]1[C:7]2[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[S:10][C:6]=2[CH2:5][CH2:4][NH:3]1.Cl[CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24].C([O-])([O-])=O.[Na+].[Na+]>CC(C)CC(=O)C>[CH2:2]1[C:7]2[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[S:10][C:6]=2[CH2:5][CH2:4][N:3]1[CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 19758183tert-Butyl (4-chlorobutyl)carbamateHCID 694849091,2,3,4-tetrahydro[1]benzothieno[3,2-c]pyridine HCl

Product 1

HCID 865863891,1-dimethylethyl [4-(3,4-dihydro[1]benzothieno[3,2-c]pyridine-2(1H)-yl)butyl]carbamate

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 1,2,3,4-tetrahydro[1]benzothieno[3,2-c]pyridine HCl (1:1) (0.02 mol), 1,1-dimethylethyl (4chlorobutyl)carbamate (0.044 mol), Na2CO3 (0.05 mol) and KI (catalytic quantity) in 4-methyl-2-pentanone (200 ml) was stirred and refluxed overnight, then cooled to room temperature and the solvent was evaporated. The residue was washed with water and extracted with CH2Cl2. The separated organic layer was dried, filtered and the solvent evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 90/10). The desired fractions were collected and the solvent was evaporated, yielding 1,1-dimethylethyl [4-(3,4-dihydro[1]benzothieno[3,2-c]pyridine-2(1H)-yl)butyl]carbamate (interim.1).

Workup

  1. temperaturerefluxed overnight
  2. customthe solvent was evaporated
  3. washThe residue was washed with water
  4. extractionextracted with CH2Cl2
  5. customThe separated organic layer was dried
  6. filtrationfiltered
  7. customthe solvent evaporated
  8. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 90/10)
  9. customThe desired fractions were collected
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-28c7b8056258470188256ef54b7fc085
Source dataset
uspto-grants-2004_08
Patent number
US06774129B2

Reaction notes

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