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Triethylamine → (R)-N-[8-(4-Methylpiperazin-1-yl)-1,2,3,4-tetrahydro-2-naphthyl]-4-morpholinocarbonylbenzamide

HRID 1954832
Notes
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Reaction equation

HRID 1954832 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]([C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=2)=[O:8])[CH2:3][CH2:2]1.[NH2:18][C@@H:19]1[CH2:28][CH2:27][C:26]2[C:21](=[C:22]([N:29]3[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]3)[CH:23]=[CH:24][CH:25]=2)[CH2:20]1.C(N(CC)CC)C>S(Cl)(Cl)=O.C(Cl)Cl>[CH3:35][N:32]1[CH2:33][CH2:34][N:29]([C:22]2[CH:23]=[CH:24][CH:25]=[C:26]3[C:21]=2[CH2:20][C@H:19]([NH:18][C:13](=[O:15])[C:12]2[CH:11]=[CH:10][C:9]([C:7]([N:4]4[CH2:3][CH2:2][O:1][CH2:6][CH2:5]4)=[O:8])=[CH:17][CH:16]=2)[CH2:28][CH2:27]3)[CH2:30][CH2:31]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 47142364-(Morpholine-4-carbonyl)benzoic acidHCID 53960413(R)-2-amino-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 54251823(R)-N-[8-(4-Methylpiperazin-1-yl)-1,2,3,4-tetrahydro-2-naphthyl]-4-morpholinocarbonylbenzamide

Reagents, catalysts & solvents 2

HCID 6344
Dichloromethane
Solvent
HCID 24386Thionyl ChlorideSolvent

Procedure

4-Morpholinocarbonylbenzoic acid (130 mg, 0.54 mmol; described in: J. Med. Chem. 1994, 37 (26), 4538-4554) was dissolved in thionyl chloride (5 mL). When the acid was dissolved, the excess of thionyl chloride was evaporated in vacuo, the residue was treated with toluene and again the solvent was removed in vacuo. The crude acid chloride was dissolved in methylene chloride (5 mL) and added dropwise to an ice-cooled solution of (R)-2-amino-8-(4-methylpiperazine-1-yl)-1,2,3,4-tetrahydronaphthalene (120 mg, 0.49 mmol) and triethylamine (100 μL, 0.73 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 organic phase was dried (Na2SO4), filtered and evaporated in vacuo to give a crude product which was purified on a silica gel column using using chloroform/methanol/concentrated ammonium hydroxide (95:4:0.5) as the eluent. Yield: 160 mg (72%) of the title compound as white crystals: mp 124-127° C.; [α]21D -40° (c 1.0, chloroform); EIMS (70 eV) m/z (relative intensity) 462 (2, M+).

Workup

  1. dissolutionWhen the acid was dissolved
  2. customthe excess of thionyl chloride was evaporated in vacuo
  3. additionthe residue was treated with toluene
  4. customagain the solvent was removed in vacuo
  5. dissolutionThe crude acid chloride was dissolved in methylene chloride (5 mL)
  6. additionadded dropwise to an ice-
  7. additionAfter the addition
  8. washwas then washed with dilute aqueous sodium hydrogen carbonate
  9. customThe phases were separated
  10. dry with materialthe organic phase was dried (Na2SO4)
  11. filtrationfiltered
  12. customevaporated in vacuo

Sources & evidence

ORD record
ord-92eb39369ee4400da4b5402943f5d3c2
Source dataset
uspto-grants-2000_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06124283

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes