Nitrogen → HCID 57467510, compound

HRID 241587Notes

Reaction equation

HRID 241587 reaction equation
Cl[CH:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1.C(Br)C.N#N.[F:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1C#N.[NH4+].[Cl-]>O.C1COCC1>[F:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1

Participants

8

Reactant 5

HCID 947NitrogenHCID 6332Ethyl BromideHCID 25517Ammonium ChlorideHCID 678552-FluorobenzonitrileHCID 793424-chloro-N-methylpiperidine

Product 1

HCID 57467510HCID 57467510, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

800 ml of THF solution of 4-chloro-N-methylpiperidine (245 g, 1.8 mol) is drop-added slowly to 250 ml of tetrahydrofuran wherein Mg powder (55.7 g, 2.3 mol) and small amount of ethyl bromide are added under coverage of N2. After completion of drop-addition, a reaction is carried out at reflux for one hour. The reaction solution is drop-added 440 ml of THF solution of 2-fluorobenzonitrile (222 g, 1.8 mol). After completion of drop-addition, a reaction is carried out at reflux for 3 hours and at room temperature for 13 hours; thereafter the reaction solution is poured into 2.3 L of water containing 700 g of NH4Cl and then reflux for 2 hours. The reaction solution is cooled and then is extracted with diethyl ether, and the extracting solutions are combined, evaporated to dryness and fractioned. The fractions at 124° C. are collected to obtain 224 g of a product.

Workup

  1. additionAfter completion of drop-addition
  2. temperatureat reflux for one hour
  3. additionAfter completion of drop-addition
  4. temperaturereflux for 2 hours
  5. temperatureThe reaction solution is cooled
  6. extractionis extracted with diethyl ether
  7. customevaporated to dryness
  8. customThe fractions at 124° C. are collected

Sources & evidence

ORD record
ord-455551ccf8cd47fea15be2e4ee8a47ae
Source dataset
uspto-grants-2014_02
Patent number
US08653069B2

Reaction notes

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