Hydrochloric Acid → HCID 20256310, compound

HRID 637845Notes

Reaction equation

HRID 637845 reaction equation
BrCCC1C([Cl:10])=CC(Cl)=[CH:6][C:5]=1[O:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Cl:20])[C:14]=1CCBr.Cl.[CH:25]1([NH2:31])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>CO>[ClH:10].[Cl:19][C:17]1[CH:18]=[C:13]([CH:14]=[C:15]([Cl:20])[CH:16]=1)[O:12][CH2:5][CH2:6][NH:31][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7965CyclohexylamineHCID 86739921HCID 86739921, compound

Product 1

HCID 20256310HCID 20256310, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 27.2 g (0.1 mole) of 2-bromoethyl-3,5-dichlorophenyl ether in 300 ml of cyclohexylamine (excess) was stirred overnight at room temperature. The reaction mixture was filtered and the filtrate stripped to dryness on a rotary evaporator. The residue was partitioned between chloroform and water and between chloroform and 10% sodium hydroxide. The chloroform layer was evaporated to dryness leaving an oil (free base). The oil was dissolved in methanol and reacted with ethereal hydrogen chloride to give 25.8 g (94.2%) solid, m.p. 216.5°-220° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate stripped to dryness on a rotary evaporator
  3. customThe residue was partitioned between chloroform and water and between chloroform and 10% sodium hydroxide
  4. customThe chloroform layer was evaporated to dryness
  5. customleaving an oil (free base)

Sources & evidence

ORD record
ord-2a803067f25b476a825b8cee2f79a5c0
Source dataset
uspto-grants-1985_12
Patent number
US04558155

Reaction notes

Loading…