Triethylamine → HCID 54046917, compound

HRID 1954823Notes

Reaction equation

HRID 1954823 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=O)(=[O:4])=[O:3].[NH2:15][C@@H:16]1[CH2:25][CH2:24][C:23]2[C:18](=[C:19]([N:26]3[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]3)[CH:20]=[CH:21][CH:22]=2)[CH2:17]1.C(N(CC)CC)C>S(Cl)(Cl)=O.C(Cl)Cl>[CH3:32][N:29]1[CH2:30][CH2:31][N:26]([C:19]2[CH:20]=[CH:21][CH:22]=[C:23]3[C:18]=2[CH2:17][C@H:16]([NH:15][C:8](=[O:10])[C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[O:5][S:2]([CH3:1])(=[O:3])=[O:4])[CH2:25][CH2:24]3)[CH2:27][CH2:28]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 261628HCID 261628, compoundHCID 53960413(R)-2-amino-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 54046917HCID 54046917, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 2-methanesulfonyloxybenzoic acid (0.30 g, 1.4 mmol; described in: Looker, J. H.; Hayes, C. H.; Thatcher, D. N. J. Am. Chem. Soc. 1957, 79, 741-4) in thionyl chloride (10 mL) was heated at 40° C. for 45 min. The excess of thionyl chloride was evaporated in vacuo, the residue was treated with toluene and again the solvent was removed in vacuo. Crude acid chloride (120 mg, 0.49 mmol) was dissolved in methylene chloride (5 mL) and added dropwise to an ice-cooled solution of (R)-2-amino-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene (120 mg, 0.47 mmol) and triethylamine (98 μL, 0.72 mmol) in methylene chloride (20 mL). After the addition, the reaction was allowed to stir at ambient temperature for 15 min and was then washed with dilute aqueous sodium hydrogen carbonate. The phases were separated and the combined organic phases were dried (Na2SO4), filtered and evaporated in vacuo to give a crude product which was purified on a silica gel column using chloroform/ethanol saturated with NH3 (100:3) as the eluent. Yield: 110 mg (55%) of the title compound as white crystals: mp 144-145° C.; [α]21D -7.1° (c 1.0, chloroform); EIMS (70 eV) m/z (relative intensity) 443 (10, M+).

Workup

  1. customThe excess of thionyl chloride was evaporated in vacuo
  2. additionthe residue was treated with toluene
  3. customagain the solvent was removed in vacuo
  4. additionAfter the addition
  5. washwas then washed with dilute aqueous sodium hydrogen carbonate
  6. customThe phases were separated
  7. dry with materialthe combined organic phases were dried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-29367ff6840d4fee876a7a62a31997fd
Source dataset
uspto-grants-2000_09
Patent number
US06124283

Reaction notes

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