Sodium Chloride → HCID 22401907, compound

HRID 260607Notes

Reaction equation

HRID 260607 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).

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-8f655df2e76048e581ecd4b40ea55a9e
Source dataset
uspto-grants-1996_06
Patent number
US05527955

Reaction notes

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