Hydrochloric Acid → trans-3,4-dichloro-N-(2-hydroxycycloheptyl)aniline hydrochloride salt

HRID 237012Notes

Reaction equation

HRID 237012 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH2:5].[CH:10]12[O:17][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2.Cl>>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH:5][C@@H:10]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]1[OH:17]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 72573,4-DichloroanilineHCID 675128-Oxabicyclo(5.1.0)octane

Product 1

HCID 70591975trans-3,4-dichloro-N-(2-hydroxycycloheptyl)aniline hydrochloride salt

Procedure

A solution of 3,4-dichloroaniline, cycloheptene oxide, and concentrated HCl (2 ml.) is heated at reflux temperature for seven (7) days. The unreacted epoxide is evaporated and the residue is treated with excess ethereal HCl, and a syrup results. This is washed with ether. The residue is crystallized and recrystallized from methanol/ether (1/5.5, v/v) to give trans-3,4-dichloro-N-(2-hydroxycycloheptyl)aniline, hydrochloride salt.

Workup

  1. customThe unreacted epoxide is evaporated
  2. additionthe residue is treated with excess ethereal HCl
  3. customa syrup results
  4. washThis is washed with ether
  5. customThe residue is crystallized
  6. customrecrystallized from methanol/ether (1/5.5

Sources & evidence

ORD record
ord-c8620e4b1c144a4488e1c20e38ac878b
Source dataset
uspto-grants-1979_06
Patent number
US04159339

Reaction notes

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