Hydrochloric Acid → HCID 67902673, compound

HRID 1638348Notes

Reaction equation

HRID 1638348 reaction equation
[CH3:1][N:2]([CH3:11])[CH:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][NH:6]1)[CH3:4].[Cl:12][C:13]1[CH:14]=[C:15]([CH2:20][C:21](O)=[O:22])[CH:16]=[CH:17][C:18]=1[Cl:19].C1(N=C=NC2CCCCC2)CCCCC1.Cl>CC(C)=O.CCOCC.C(Cl)Cl>[ClH:12].[Cl:12][C:13]1[CH:14]=[C:15]([CH2:20][C:21]([N:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH:5]2[CH:3]([N:2]([CH3:1])[CH3:11])[CH3:4])=[O:22])[CH:16]=[CH:17][C:18]=1[Cl:19]

Participants

8

Reactant 4

HCID 313Hydrochloric Acid2×HCID 10868DicyclohexylcarbodiimideHCID 798743,4-Dichlorophenylacetic acidHCID 14810988HCID 14810988, compound

Product 1

HCID 67902673HCID 67902673, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

Gr 1.6 (moles 0.01) of 2-(1-dimethylaminoethyl) piperidine and gr2.25 (moles 0.011) of 3,4-dichlorophenylacetic acid, dissolved in 20 ml. of CH2Cl2 were added with gr.3.1 (moles 0.015) of dicyclohexylcarbodiimide dissolved in 20 ml. of CH2Cl2. After 48 hours standing, the reaction mixture was worked up as in Ex. No 1 C) giving 2.8 g. of oily mixture of diastereoisomers. This was chromatographed on g.60 of silicagel, eluting with CH2Cl2 containing increasing amounts of methanol (0.2% to 1%). The fast moving diastereoisomer A was so obtained. It was dissolved in acetone and transformed into the hydrochloride by acidifying with HCl dissolved in ether. The precipitate was crystallized from acetone.

Workup

  1. dissolutiondissolved in 20 ml
  2. customNo 1 C) giving 2.8 g
  3. additionof oily mixture of diastereoisomers
  4. customThis was chromatographed on g.60 of silicagel
  5. washeluting with CH2Cl2 containing
  6. temperatureincreasing amounts of methanol (0.2% to 1%)
  7. customThe fast moving diastereoisomer A was so obtained
  8. customThe precipitate was crystallized from acetone

Sources & evidence

ORD record
ord-d47ed2c52b824224b95b7489e47d0f60
Source dataset
uspto-grants-1989_11
Patent number
US04879300

Reaction notes

Loading…