Sodium Carbonate → 1-Naphthalenol, 6-[bis[2-(2-thienyl)ethyl]amino]-5,6,7,8-tetrahydro-, (6S)-

HRID 1472789Notes

Reaction equation

HRID 1472789 reaction equation
[NH2:1][C@H:2]1[CH2:11][CH2:10][C:9]2[C:8]([OH:12])=[CH:7][CH:6]=[CH:5][C:4]=2[CH2:3]1.CS(O[CH2:18][CH2:19][C:20]1[S:21][CH:22]=[CH:23][CH:24]=1)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C(C)=CC=CC=1>[S:21]1[CH:22]=[CH:23][CH:24]=[C:20]1[CH2:19][CH2:18][N:1]([C@H:2]1[CH2:11][CH2:10][C:9]2[C:8]([OH:12])=[CH:7][CH:6]=[CH:5][C:4]=2[CH2:3]1)[CH2:18][CH2:19][C:20]1[S:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 30477232-(2-Thienyl)ethyl methanesulphonateHCID 68185804(6S)-6-Amino-5,6,7,8-tetrahydronaphthalen-1-ol

Product 1

HCID 712588171-Naphthalenol, 6-[bis[2-(2-thienyl)ethyl]amino]-5,6,7,8-tetrahydro-, (6S)-Yield 63.6%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

5.0 g of (S)-5,6,7,8-tetrahydro-6-amino-1-naphthol, 2.2 g of 2-(2-thienyl)ethyl methane-sulfonate, 4.8 g of sodium carbonate and 100 ml of xylene were mixed to form a mixture, and the mixture was refluxed for 48 h to 50 h. The mixture was cooled to room temperature, and washed with an appropriate amount of water. Active carbon was added to decolorize the mixture. The mixture was filtered and left standing. An organic phase was reserved and concentrated under vacuum to obtain a residue. The residue was purified by column chromatography to obtain 1.3 g of (S)-5,6,7,8-tetrahydro-6-[N,N-bis[(2-thienyl)ethyl]]amino-1-naphthol.

Workup

  1. temperaturethe mixture was refluxed for 48 h to 50 h
  2. washwashed with an appropriate amount of water
  3. additionActive carbon was added
  4. filtrationThe mixture was filtered
  5. waitleft standing
  6. concentrationconcentrated under vacuum
  7. customto obtain a residue
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-a858438c72d14b55a4bc05b12a84abcb
Source dataset
uspto-grants-2015_04
Patent number
US09012660B2

Reaction notes

Loading…