Dichloromethane → HCID 58110678, compound

HRID 2096995Notes

Reaction equation

HRID 2096995 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1.ClC[CH2:13][CH2:14][CH2:15][CH2:16][C:17](Cl)=[O:18].C(Cl)[Cl:21]>N1C=CC=CC=1>[Cl:21][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([NH:10][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH3:9])=[O:18]

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 880146-Chlorohexanoyl chlorideHCID 1230631-(4-Fluorophenyl)ethylamine

Product 1

HCID 58110678HCID 58110678, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1-(4-fluorophenyl)ethanamine 15b (5.0 g, 35.9 mmol) in a mixture of 10 mL of DCM and 14.5 mL of pyridine, with ice cooling, was added dropwise a solution of 6-chlorohexanoyl chloride 15a in 20 mL of DCM. After the addition was compete, cooling was removed and the resulting precipitate was stirred overnight. The reaction mixture was diluted with 100 mL of ther and washed with 100 mL of 1M HCl. The organic phase was dried over MgSO4 and concentrated to furnish 9.2 g of crude 5-chloro-N-(1-(4-fluorophenyl)ethyl)pentanamide 15c which was used in the next step without purification.

Workup

  1. additionAfter the addition
  2. temperaturecooling
  3. customwas removed
  4. additionThe reaction mixture was diluted with 100 mL of ther and
  5. washwashed with 100 mL of 1M HCl
  6. dry with materialThe organic phase was dried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-34c3b58d26e348f7a5648d0eafa6f0ae
Source dataset
uspto-grants-2013_05
Patent number
US08450343B2

Reaction notes

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