Sodium Iodide → HCID 67820118, compound

HRID 1707283Notes

Reaction equation

HRID 1707283 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][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[C:7]([CH3:26])[NH:6][C:5]=1OCOCC[Cl:32])(=[O:3])[CH3:2].[I-].[Na+].Cl.[C:36]1([C:42]2([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>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][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:20])=[C:7]([CH3:26])[NH:6][C:5]=1[CH2:22][O:21][CH2:19][CH2:8][N:45]1[CH2:44][CH2:43][C:42]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH2:47][CH2:46]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 30475044,4-Diphenylpiperidine hydrochlorideHCID 18963000HCID 18963000, compound

Product 1

HCID 67820118HCID 67820118, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

8.5 g (19 mmol) 3-acetyl-5-tert-butoxycarbonyl-2-(2-chloro-1-ethoxy)methoxy-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-pyridine are reacted first with 5.6 g (38 mmol) sodium iodide, as described for starting compound B, and then with 10.3 g (36 mmol) 4,4-diphenylpiperidine hydrochloride. Working up is carried out as described for starting compound B. The crude product is chromatographed with toluene/acetone=9/1. The product thus obtained is taken up in 50 ml diethyl ether. The title compound is precipitated by addition of ethereal hydrochloric acid. Yield: 11 g (84%). M.p. 175°-177° C. (diethyl ether).

Workup

  1. customThe crude product is chromatographed with toluene/acetone=9/1
  2. customThe product thus obtained
  3. customThe title compound is precipitated by addition of ethereal hydrochloric acid

Sources & evidence

ORD record
ord-7238e8552bea4b748c7cd9666a72d11e
Source dataset
uspto-grants-1994_10
Patent number
US05352684

Reaction notes

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