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

HRID 427134Notes

Reaction equation

HRID 427134 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH2:5].Cl.[CH:11]12[O:18][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2>>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH:5][C@@H:11]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]1[OH:18]

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 (200 g., 1.23 mole), cycloheptene oxide (400 ml.), and concentrated HCl (2 ml.) is heated at reflux temperature for seven (7) days. The unreacted epoxide is evaporated at 60° C. and the residue is treated with excess ethereal HCl, and a syrup results. This is washed with 1000 ml. 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 at 60° C.
  2. additionthe residue is treated with excess ethereal HCl
  3. customa syrup results
  4. washThis is washed with 1000 ml
  5. customThe residue is crystallized
  6. customrecrystallized from methanol/ether (1/5,5

Sources & evidence

ORD record
ord-c012ff7ff5554ff2a673be1713bf6917
Source dataset
uspto-grants-1979_10
Patent number
US04172898

Reaction notes

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