Sodium Iodide → HCID 22992850, compound

HRID 1953064Notes

Reaction equation

HRID 1953064 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:12](=[O:13])[C:11]2[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:10]=2[O:9][CH:8]=[C:7]1[Cl:19].N1C=CC=CC=1[N:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.[I-].[Na+].C([N:36]([CH2:39][CH3:40])[CH2:37][CH3:38])C.[CH3:41]N(C)C=O>>[Cl:19][C:7]1[N:6]([CH2:5][CH2:4][CH2:3][CH2:2][N:36]2[CH2:37][CH2:38][CH:41]([C:31]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)[CH2:40][CH2:39]2)[C:12](=[O:13])[C:11]2[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:10]=2[O:9][CH:8]=1

Participants

6

Reactant 5

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 8471TriethylamineHCID 8177592-piperidin-1-ylpyridineHCID 22992851HCID 22992851, compound

Product 1

HCID 22992850HCID 22992850, compoundYield 93%

Procedure

169 mg of the 4-(4-chlorobutyl)-3,8-dichloro-4,5-dihydro-1,4-benzoxazepin-5-one synthesized by the method of Example 17 described in International Publication WO96/24594 was dissolved in 3 ml of dimethylformamide, then 129 mg (1.5 equivalents) of 1-(2-pyridyl)piperadine, 158 mg (2 equivalents) of sodium iodide, and 106 mg (2 equivalents) of triethylamine were added and the resultant mixture agitated at 80° C. for 6 hours. This was treated and refined in the same way as Example 13 to obtain 219 mg of the above-referenced compound (yield 93%). Note that the dichloride was obtained by making a dichloride by an ordinary method, then recrystallizing from a mixed solvent of methanol, chloroform, and ether.

Workup

  1. additionThis was treated

Sources & evidence

ORD record
ord-ae38826c430f4c7cbfd7c1128a190d27
Source dataset
uspto-grants-2000_09
Patent number
US06114522

Reaction notes

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