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

HRID 1882313Notes

Reaction equation

HRID 1882313 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-51cc37b37f844c449f5ca773cf4c60ec
Source dataset
uspto-grants-2012_11
Patent number
US08318973B2

Reaction notes

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