Triethylamine → HCID 53996705, compound

HRID 1954826Notes

Reaction equation

HRID 1954826 reaction equation
[CH2:1]([O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[NH2:15][C@@H:16]1[CH2:25][CH2:24][C:23]2[C:18](=[C:19]([CH: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.C(OCC)(=O)C>[CH3:32][N:29]1[CH2:30][CH2:31][CH:26]([C:19]2[CH:20]=[CH:21][CH:22]=[C:23]3[C:18]=2[CH2:17][C@H:16]([NH:15][C:10](=[O:12])[C:9]2[CH:8]=[CH:7][C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:14][CH:13]=2)[CH2:25][CH2:24]3)[CH2:27][CH2:28]1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 729714-Butoxybenzoic acidHCID 54282228HCID 54282228, compound

Product 1

HCID 53996705HCID 53996705, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 24386Thionyl ChlorideSolvent

Procedure

4-Butoxybenzoic acid (0.16 g, 0.8 mmol) was dissolved in thionyl chloride (3 mL) and refluxed for 30 minutes. The excess of thionyl chloride was removed in vacuo with toluene. The residue was dissolved in methylene chloride (5 mL) and added dropwise to an ice cold solution of (R)-2-amino-8-(1-methylpiperidin-4-yl)-1,2,3,4-tetrahydronaphthalene (0.15 g, 0.6 mmol) and triethylamine (92 mg, 0.9 mmol) in methylene chloride (5 mL). The mixture was stirred for 30 minutes and was then diluted with ethyl acetate, washed with ammonia (2 is M) and dried (MgSO4). The solvent was removed in vacuo. The residue was purified by flash chromatography on silica gel using methylene chloride/ethanol 5:1, containing 0.5% of ammonia, as the eluent. The title compound was obtained as white crystals. Yield 170 mg (50%): mp 162-164° C.; [α]21D -2° (c 0.5, CHCl3); EIMS (70 eV) m/z (relative intensity) 420 (40, M+).

Workup

  1. temperaturerefluxed for 30 minutes
  2. customThe excess of thionyl chloride was removed in vacuo with toluene
  3. dissolutionThe residue was dissolved in methylene chloride (5 mL)
  4. washwashed with ammonia (2 is M)
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in vacuo
  7. customThe residue was purified by flash chromatography on silica gel
  8. additioncontaining 0.5% of ammonia

Sources & evidence

ORD record
ord-a16fcc2d444c46a1be3e96c2adad1561
Source dataset
uspto-grants-2000_09
Patent number
US06124283

Reaction notes

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