Hydrochloric Acid → HCID 68453948, compound

HRID 2353603Notes

Reaction equation

HRID 2353603 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][OH:18])=[CH:11][C:10]=1[O:19][CH3:20])(C)(C)C.Cl>C(O)(=O)C>[NH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][OH:18])=[CH:11][C:10]=1[O:19][CH3:20]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68452888[4-(2-Hydroxyethoxy)-2-methoxybenzyl]carbamic acid tert-butyl ester

Product 1

HCID 68453948HCID 68453948, compoundYield 9.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

The above [4-(2-hydroxy-ethoxy)-2-methoxy-benzyl]-carbamic acid tert-butyl ester (10.3 mg, 0.35 mmol) is treated with 37% aq. HCl (0.1 mL) and acetic acid (1 mL) for 1.5 h at rt. The solvents are removed by lyophilisation. The residue is dissolved in 2 N aq. NaOH (1 mL) and ethanol (0.25 mL) and heated to 80° C. for 1 h. The mixture is cooled to rt and extracted twice with EA. The organic extracts are combined, dried over Na2SO4, filtered and evaporated to give 2-(4-aminomethyl-3-methoxy-phenoxy)-ethanol (6.4 mg) as a beige oil. LC-MS: tR=0.58 min, [M+1]+=198.11.

Workup

  1. customThe solvents are removed by lyophilisation
  2. dissolutionThe residue is dissolved in 2 N aq. NaOH (1 mL)
  3. temperatureThe mixture is cooled to rt
  4. extractionextracted twice with EA
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-6748cbd9a166448881ce1776001f35f6
Source dataset
uspto-grants-2010_07
Patent number
US07750040B2

Reaction notes

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