Triethylamine → Amitriptyline

HRID 977047

反応式

HRID 977047 の反応式
[CH:1]1[C:6](C(O)=O)=[CH:5][C:4]([C:10]2C3C=CC(O)=CC=3OC3[C:11]=2[CH:12]=[CH:13][C:14]([CH:16]=3)=O)=[C:3](C(O)=O)[CH:2]=1.ON1[C:34](=O)[CH2:33][CH2:32][C:31]1=O.C1(N=C=NC2CCCCC2)CCCCC1.[CH2:52]([N:54]([CH2:57]C)[CH2:55][CH3:56])C>CN(C=O)C>[CH3:57][N:54]([CH2:55][CH2:56][CH:31]=[C:32]1[C:5]2[CH:6]=[CH:1][CH:2]=[CH:3][C:4]=2[CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:16]=[CH:34][C:33]1=2)[CH3:52]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 2725051ST51005980

生成物 1

HCID 2160Amitriptyline

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

6-Carboxyfluorescein (1.00 g, 2.66 mmol) was dissolved in 8 mL DMF, 306 mg (2.66 mmol) of N-hydroxysuccinimide (HOSu) was added, 549 mg (2.66 mmol) of 1,3-dicyclohexylcarbodiimide (DCC) was added, and the reaction stirred for 17 hours, under N2, in the dark. The reaction was then vacuum filtered, filtrate combined with 784 mg (2.65 mmol) of 2-aminoimipramine (26c), 0.56 mL (4.0 mmol) of triethylamine, and 4.0 mL DMF, and reaction allowed to stir 4 days under N2, in the dark. Reaction solvents were removed in vacuo and residue purified on reverse phase C18 preparative (1 mm) TLC plates, eluting with H2O/THF/HOAc (40/60/0.4) followed by preparative HPLC on a Waters mbondapak C18 column (19 mm×150 mm), eluting with H2O/THF/HOAc (35/65/0.4) at a flow rate of 7.0 mL/minute to yield 410 mg (24%) of the desired tracer (27) as an orange powder; mass spec (FAB) (M+H)+ 654.

後処理

  1. filtrationvacuum filtered
  2. stirringto stir 4 days under N2, in the dark
  3. customReaction solvents
  4. customwere removed in vacuo and residue
  5. custompurified on reverse phase C18 preparative (1 mm) TLC plates
  6. washeluting with H2O/THF/HOAc (40/60/0.4)
  7. washeluting with H2O/THF/HOAc (35/65/0.4) at a flow rate of 7.0 mL/minute

出典と根拠

ORDレコード
ord-af4a453f212144719d9bbba75fba989f
出典データセット
uspto-grants-1997_03
特許番号
US05614419

関連ノート

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