Sodium Iodide → 1-[(Benzo-1,4-dioxan-2-yl)-methyl]-4-(5-chlorobenzimidazol-2-on-1-yl)-piperidine hydrochloride

HRID 2417799Notes

Reaction equation

HRID 2417799 reaction equation
Br[CH2:2][CH:3]1[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][CH2:4]1.[Cl:13][C:14]1[CH:29]=[CH:28][C:17]2[N:18]([CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[C:19](=[O:21])[NH:20][C:16]=2[CH:15]=1.[I-].[Na+].C(OC(C)C)(C)C>CN(C)C=O.C(N(CC)CC)C>[ClH:13].[O:8]1[C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][CH2:4][CH:3]1[CH2:2][N:25]1[CH2:24][CH2:23][CH:22]([N:18]2[C:17]3[CH:28]=[CH:29][C:14]([Cl:13])=[CH:15][C:16]=3[NH:20][C:19]2=[O:21])[CH2:27][CH2:26]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 7914Diisopropyl EtherHCID 983332-Bromomethyl-1,4-benzodioxaneHCID 1046075-Chloro-1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one

Product 1

HCID 204467121-[(Benzo-1,4-dioxan-2-yl)-methyl]-4-(5-chlorobenzimidazol-2-on-1-yl)-piperidine hydrochloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

2.3 g of 2-bromomethyl-1,4-benzodioxane, 2.2 g of 4-(5-chlorobenzimidazol-2-on-1-yl)-piperidine, 1.4 ml of triethylamine and 0.3 g of sodium iodide were stirred in 25 ml of dry dimethylformamide at room temperature for 60 hours and the mixture was then poured onto water; diisopropyl ether was added and the mixture was stirred vigorously for 2 hours. The product which had precipitated was filtered off with suction, washed with water and diisopropyl ether and dried; the free base thus obtained has a melting point of 226°-228° C.

Workup

  1. additionthe mixture was then poured onto water
  2. customThe product which had precipitated
  3. filtrationwas filtered off with suction
  4. washwashed with water and diisopropyl ether
  5. customdried
  6. customthe free base thus obtained

Sources & evidence

ORD record
ord-dd5f266ccc9f47fcaabe5a990a46cadd
Source dataset
uspto-grants-1984_09
Patent number
US04470989

Reaction notes

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