Triethylamine → HCID 54382107, compound

HRID 1954829Notes

Reaction equation

HRID 1954829 reaction equation
[S:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[NH2:16][C@@H:17]1[CH2:26][CH2:25][C:24]2[C:19](=[C:20]([N:27]3[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]3)[CH:21]=[CH:22][CH:23]=2)[CH2:18]1.C(N(CC)CC)C>S(Cl)(Cl)=O.C(Cl)Cl>[CH3:33][N:30]1[CH2:31][CH2:32][N:27]([C:20]2[CH:21]=[CH:22][CH:23]=[C:24]3[C:19]=2[CH2:18][C@H:17]([NH:16][C:11](=[O:13])[C:10]2[CH:9]=[CH:8][C:7]([N:4]4[CH2:3][CH2:2][S:1][CH2:6][CH2:5]4)=[CH:15][CH:14]=2)[CH2:26][CH2:25]3)[CH2:28][CH2:29]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 18475716HCID 18475716, compoundHCID 53960413(R)-2-amino-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 54382107HCID 54382107, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 24386Thionyl ChlorideSolvent

Procedure

4-Thiomorpholinobenzoic acid (0.25 g, 1.1 mmol) was dissolved in thionyl chloride (25 mL). The excess of thionyl chloride was immediately evaporated in vacuo, the residue was treated with toluene and again the solvent was removed in vacuo. Crude acid chloride (107 mg, 0.44 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 (104 mg, 0.42 mmol) and triethylamine (68 μL, 0.87 mmol) in methylene chloride (35 mL). After the addition the reaction was allowed to stir at ambient temperature for 15 min and then washed with diluted aqueous sodium hydrogen carbonate. The phases were separated and the organic phase was dried (Na2SO4), filtered and evaporated in vacuo to give a crude product which was purified on a silica gel column using chloroform/methanol/concentrated ammonium hydroxide (95:5:0.5) as the eluent. Yield: 58 mg (31%) of the title compound as white crystals: mp 190-191° C.; [α]21D -86° (c 0.25, chloroform); EIMS (70 eV) m/z (relative intensity) 450 (2, M+).

Workup

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

Sources & evidence

ORD record
ord-42dce369d46e412b874f6ac2c6148e6a
Source dataset
uspto-grants-2000_09
Patent number
US06124283

Reaction notes

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