Hydrochloric Acid → 6-(4-Amino-phenoxy)hexanoic acid hydrochloride

HRID 2405180Notes

Reaction equation

HRID 2405180 reaction equation
C[O:2][C:3](=[O:20])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16]C(=O)C)=[CH:12][CH:11]=1.[ClH:21]>>[ClH:21].[NH2:16][C:13]1[CH:12]=[CH:11][C:10]([O:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:20])=[O:2])=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 497644916-(4-Acetylaminophenoxy)-hexanoic acid methyl ester

Product 1

HCID 668113476-(4-Amino-phenoxy)hexanoic acid hydrochlorideYield 55.6%

Conditions

Temperature
10 °C

Procedure

To a mixture of 6-(4-Acetylamino-phenoxy)-hexanoic acid methyl ester 65 (290 grams, 1.04 moles), in concentrated hydrochloric acid (7.12 Liter) was refluxed for 48 hours. Excess concentrated hydrochloric acid was distilled off in vacuum and filtered hot. The mixture was cooled to 10° C., filtered and dried give pure 66 (150 grams, 55.6%) as a brown powder. The melting point was found to be 155-160° C.

Workup

  1. distillationExcess concentrated hydrochloric acid was distilled off in vacuum
  2. filtrationfiltered hot
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-c3054e9a46f34c39802c39166dc9688e
Source dataset
uspto-grants-2014_08
Patent number
US08802892B2

Reaction notes

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