Sodium Chloride → HCID 22401907, compound

HRID 1109559Notes

Reaction equation

HRID 1109559 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]#[N:7].[CH2:8]([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)C(C)C)(C)C.[Cl-].[Na+]>CN(C)C=O.O>[CH2:16]([N:15]([CH2:2][CH2:3][CH2:4][CH2:5][C:6]#[N:7])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 7656DibenzylamineHCID 794355-BromopentanenitrileHCID 81531Diisopropylethylamine

Product 1

HCID 22401907HCID 22401907, compoundYield 108.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
110 °C

Procedure

A solution of 5-bromopentanonitrile (16.20 g) in dry dimethylformamide (100 ml) was added dropwise over 15 minutes to a stirred solution of dibenzylamine (19.73 g) and N,N-diisopropylethylamine (35 ml 26 g) in dry dimethylformamide (100 ml). The solution was heated (oil bath 110° C.) for 4 hours and was allowed to cool. The solution was poured onto a mixture of saturated aqueous sodium chloride (400 ml) and water (400 ml) and the mixture was extracted with ether (2×200 ml). The extracts were dried (Na2SO4) and concentrated in vacuo to give a mobile oil (30.32 g). The oil was chromatographed on silica with eluant diethyl ether to give the title compound (23.17 g) as an oil which was used without further purification in Example 14.

Workup

  1. temperatureto cool
  2. extractionthe mixture was extracted with ether (2×200 ml)
  3. dry with materialThe extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-10ac445166d9474ea3574c7267a9f1c1
Source dataset
uspto-grants-1994_06
Patent number
US05321047

Reaction notes

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