Sodium Iodide → HCID 67820037, compound

HRID 1707282Notes

Reaction equation

HRID 1707282 reaction equation
[C:1]([C:4]1[CH:5]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-:30])=[O:29])[CH:23]=2)[C:6]([C:12](=[O:21])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]Br)=[C:7]([CH3:11])[NH:8][C:9]=1[CH3:10])(=[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:1]([C:4]1[CH:5]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-:30])=[O:29])[CH:23]=2)[C:6]([C:12](=[O:21])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:43]2[CH2:44][CH2:45][C:40]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[CH2:41][CH2:42]2)=[C:7]([CH3:11])[NH:8][C:9]=1[CH3:10])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 5238Sodium IodideHCID 30475044,4-Diphenylpiperidine hydrochlorideHCID 18962952HCID 18962952, compound

Product 1

HCID 67820037HCID 67820037, compound

Procedure

10 g (21 mmol) 5-acetyl-3-(8-bromo-octanoyl)-1,4-dihydro-2,6-dimethyl-4(3-nitrophenyl)-pyridine are reacted first with 6.3 g (42 mmol) sodium iodide and then with 11. 5 g (40 mmol) 4,4-diphenylpiperidine hydrochloride, as described for starting compound B. Working up is carried out as described for starting compound B. The crude product is chromatographed with increasing polarity, first with toluene/acetone=9/1 and finally with toluene/acetone =6/4. The product thus obtained is recrystallized from 70 ml acetonitrile. The title compound is obtained as a yellow solid. Yield: 11 g (82%). M.p. 141°-145° C. (acetonitrile).

Workup

  1. customThe crude product is chromatographed
  2. temperaturewith increasing polarity
  3. customThe product thus obtained
  4. customis recrystallized from 70 ml acetonitrile

Sources & evidence

ORD record
ord-21ced9a32f0e43e0bb6702d9966dfb1c
Source dataset
uspto-grants-1994_10
Patent number
US05352684

Reaction notes

Loading…