Sodium Iodide → HCID 18962947, compound

HRID 1707281Notes

Reaction equation

HRID 1707281 reaction equation
[C:1]([C:4]1[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=2)[C:8]([C:19](=[O:21])[CH3:20])=[C:7]([CH3:22])[NH:6][C:5]=1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]Br)(=[O:3])[CH3:2].[I-].[Na+].[ClH:32].[C:33]1([C:39]2([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(#N)C.C(OCC)C>[ClH:32].[C:1]([C:4]1[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=2)[C:8]([C:19](=[O:21])[CH3:20])=[C:7]([CH3:22])[NH:6][C:5]=1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][N:42]1[CH2:43][CH2:44][C:39]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH2:40][CH2:41]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 30475044,4-Diphenylpiperidine hydrochlorideHCID 18962993HCID 18962993, compound

Product 1

HCID 18962947HCID 18962947, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

3.5 g (7.8 mmol) 3,5-diacetyl-1,4-dihydro-2-(6-bromohexyl)6-methyl-4-(3-nitrophenyl) -pyridine are reacted first with 2.3 g (15.6 mmol) sodium iodide, as described for starting compound B, and then with 4.3 g (15.6 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 5 ml acetonitrile and the mixture is diluted with 5 ml diethyl ether. The title compound is precipitated by addition of ethereal hydrochloric acid. Yield: 3 g (61%). M.p. 166°-167° C. (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-a652cdc2ab294636966117f50f8f219b
Source dataset
uspto-grants-1994_10
Patent number
US05352684

Reaction notes

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