Hydrochloric Acid → 2-​Naphthalenamine, 1,​2,​3,​4-​tetrahydro-​5-​methoxy-​N-​propyl-​, hydrochloride (1:1)

HRID 875249Notes

Reaction equation

HRID 875249 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][C@@H:8]([NH:14][CH2:15][CH2:16][CH3:17])[CH2:9]2>>[ClH:1].[CH3:2][O:3][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][CH:8]([NH:14][CH2:15][CH2:16][CH3:17])[CH2:9]2

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 10656511(2R)-1,2,3,4-Tetrahydro-5-methoxy-N-propyl-2-naphthalenamine

Product 1

HCID 125811632-​Naphthalenamine, 1,​2,​3,​4-​tetrahydro-​5-​methoxy-​N-​propyl-​, hydrochloride (1:1)

Conditions

Temperature
20 °C

Procedure

Aqueous HCl 37% w:w (1.1 eq) is added dropwise under reflux for ˜5 min into the mixture obtained to precipitate the N-propyl MAT.HCl. The suspension is cooled down to 20° C. (Tramp=−20° C./h). The suspension is post-stirred at 20° C. for minimum 30 min and filtered. The cake is washed twice with EtOAc (2×1 vol.). The wet solid is dried under vacuum at 40° C. giving an off white solid. Yield: 95.0% from (III)

Workup

  1. additionis added dropwise
  2. temperatureunder reflux for ˜5 min into the mixture
  3. customobtained
  4. customto precipitate the N-propyl MAT
  5. filtrationfiltered
  6. washThe cake is washed twice with EtOAc (2×1 vol.)
  7. customThe wet solid is dried under vacuum at 40° C.
  8. customgiving an off white solid

Sources & evidence

ORD record
ord-3028891c0712471197f502b6d952952c
Source dataset
uspto-grants-2015_03
Patent number
US08981121B2

Reaction notes

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