Sodium Iodide → HCID 18962981, compound

HRID 1707279Notes

Reaction equation

HRID 1707279 reaction equation
[C:1]([C:4]1[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:11]=2[Cl:17])[C:8]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[C:7]([CH3:25])[NH:6][C:5]=1[CH2:26][CH2:27][CH2:28][CH2:29]Cl)(=[O:3])[CH3:2].[I-].[Na+].Cl.[C:34]1([C:40]2([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(O)(C)C>[ClH:16].[C:1]([C:4]1[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:11]=2[Cl:17])[C:8]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])=[C:7]([CH3:25])[NH:6][C:5]=1[CH2:26][CH2:27][CH2:28][CH2:29][N:43]1[CH2:44][CH2:45][C:40]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH2:41][CH2:42]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 30475044,4-Diphenylpiperidine hydrochlorideHCID 18962946HCID 18962946, compound

Product 1

HCID 18962981HCID 18962981, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

5.6 g (12.2 mmol) 3-acetyl-5-tert-butoxycarbonyl-1,4-dihydro-4-(2,3-dichlorophenyl)-2-(4-chlorobutyl)-6-methyl-pyridine are reacted first with 3.6 g (24.4 mmol) sodium iodide, as described for starting compound B, and then with 6 g (21 mmol) 4,4-diphenylpiperidine hydrochloride. Working up is carried out as described for starting compound B. The crude product is chromatographed with toluene/acetone=8/2. The product thus obtained is taken up in 30 ml isopropanol. The title compound is precipitated by addition of ethereal hydrochloric acid. Yield: 5.2 g (60%). M.p. 154°-156° C. decomp. (acetonitrile).

Workup

  1. customThe crude product is chromatographed with toluene/acetone=8/2
  2. customThe product thus obtained
  3. customThe title compound is precipitated by addition of ethereal hydrochloric acid

Sources & evidence

ORD record
ord-d4c494680bf947e18aacabf5bf958d39
Source dataset
uspto-grants-1994_10
Patent number
US05352684

Reaction notes

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