2-Fluorobenzoyl chloride → HCID 21527326, compound

HRID 1659150Notes

Reaction equation

HRID 1659150 reaction equation
[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH2:3]1.[F:13][C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16]([Cl:18])=[O:17]>C(Cl)(Cl)Cl>[ClH:18].[CH:7]1([N:4]2[CH2:5][CH2:6][CH:2]([NH:1][C:16](=[O:17])[C:15]3[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=3[F:13])[CH2:3]2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 98082-Fluorobenzoyl chlorideHCID 36700741-Cyclohexylpyrrolidin-3-amine

Product 1

HCID 21527326HCID 21527326, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To 19.5 g. (0.117 mole) of 3-amino-1-cyclohexylpyrrolidine in 100 ml. of chloroform was added dropwise 11.6 g. (0.074 mole) of o-fluorobenzoyl chloride in 100 ml. of chloroform. The solution was concentrated in vacuo and the residue partitioned between ethyl acetate containing 10% isopropyl ether and dilute hydrochloric acid. The acid layer was made basic with dilute sodium hydroxide and extracted with chloroform. The chloroform solution was dried over sodium sulfate, concentrated and the residue crystallized twice from ligroin. The yield was 13 g. (82%); m.p. at 204°-206°C.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthe residue partitioned between ethyl acetate containing 10% isopropyl ether and dilute hydrochloric acid
  3. extractionextracted with chloroform
  4. dry with materialThe chloroform solution was dried over sodium sulfate
  5. concentrationconcentrated
  6. customthe residue crystallized twice from ligroin
  7. customm.p. at 204°-206°C.

Sources & evidence

ORD record
ord-9ed648b8fd214676a372476e44d245eb
Source dataset
uspto-grants-1976_06
Patent number
US03966957

Reaction notes

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