N,N-Dimethylaniline → HCID 14405683, compound

HRID 2106644Notes

Reaction equation

HRID 2106644 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:19])=O.CN(C)C1C=CC=CC=1.[CH2:30]1[C:35]2[O:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[C:34]=2[CH2:33][CH2:32][NH:31]1>ClCCl.O>[ClH:19].[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]([N:31]2[CH2:32][CH2:33][C:34]3[C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=4[O:36][C:35]=3[CH2:30]2)=[O:16])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 949N,N-DimethylanilineHCID 24386Thionyl ChlorideHCID 47149831-Benzylpiperidine-4-carboxylic acidHCID 139252351,2,3,4-Tetrahydro[1]benzofuro[2,3-c]pyridine

Product 1

HCID 14405683HCID 14405683, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

4.4 g (20 mmol) of 1-benzyl-4-piperidinecarboxylic acid are added to 12 ml (165 mmol) of thionyl chloride, and the mixture is stirred under an inert atmosphere. Stirring is maintained for 16 h at 20° C., and the excess thionyl chloride is then evaporated off under reduced pressure. The residue is taken up with 25 ml of toluene and the mixture again evaporated under reduced pressure. The solid residue is dissolved in dichloromethane, and 5.7 ml (45 mmol) of N,N-dimethylaniline and 3.4 g (20 mmol) of 1,2,3,4-tetrahydrobenzofuro[2,3-c]pyridine (base), dissolved in 12 ml of dichloromethane, are added under argon. The mixture is stirred for 2 h at 20° C. and then poured into water. The insoluble material is isolated by filtration, washed with water and suspended in a mixture of water and ethyl acetate. This suspension is treated with ammonia solution, and the organic phase is separated off after settling has taken place, washed with water and dried. The solvent is evaporated off under reduced pressure and the amide thereby obtained dried under vacuum. The hydrochloride of the latter is prepared in 0.1N hydrochloric acid in isopropyl alcohol, and recrystallized in ethanol.

Workup

  1. stirringStirring
  2. customthe excess thionyl chloride is then evaporated off under reduced pressure
  3. customthe mixture again evaporated under reduced pressure
  4. dissolutionThe solid residue is dissolved in dichloromethane
  5. additionare added under argon
  6. stirringThe mixture is stirred for 2 h at 20° C.
  7. customThe insoluble material is isolated by filtration
  8. washwashed with water
  9. additionsuspended in a mixture of water and ethyl acetate
  10. additionThis suspension is treated with ammonia solution
  11. customthe organic phase is separated off after settling
  12. washwashed with water
  13. customdried
  14. customThe solvent is evaporated off under reduced pressure

Sources & evidence

ORD record
ord-391f0dc495564825b97cf08a7c3d32e0
Source dataset
uspto-grants-1990_06
Patent number
US04931449

Reaction notes

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