Triethylamine → Amitriptyline

HRID 1654438

반응식

HRID 1654438 반응식
[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]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 2725051ST51005980

생성물 1

HCID 2160Amitriptyline

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f2f080c2bc3648e496e1ef9e2f5f9d09
출처 데이터셋
uspto-grants-1995_04
특허 번호
US05407835

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