Dimethylamine → 1-[1-(diphenylmethyl)azetidin-3-yl]-N,N-dimethylpiperidine-4-carboxamide

HRID 426088

반응식

HRID 426088 반응식
[C:1]1([CH:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:8]2[CH2:11][CH:10]([N:12]3[CH2:17][CH2:16][CH:15]([C:18](O)=[O:19])[CH2:14][CH2:13]3)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:27][N:28](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)[CH3:29].[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.CNC.C([O-])(O)=O.[Na+]>CN(C=O)C>[C:1]1([CH:7]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:8]2[CH2:11][CH:10]([N:12]3[CH2:17][CH2:16][CH:15]([C:18]([N:28]([CH3:29])[CH3:27])=[O:19])[CH2:14][CH2:13]3)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

7

반응물 5

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 236589521-[1-(Diphenylmethyl)azetidin-3-yl]piperidine-4-carboxylic acid

생성물 1

HCID 236589531-[1-(diphenylmethyl)azetidin-3-yl]-N,N-dimethylpiperidine-4-carboxamide수율 59%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

1-[1-(Diphenylmethyl)azetidin-3-yl]piperidine-4-carboxylic acid (0.35 g, 0.9 mmol) was dissolved in DMF (8 mL) and to the solution were added TBTU (0.39 g, 1.2 mmol), DIPEA (0.21 mL, 1.2 mmol) and a solution of dimethylamine (3.0 mL, 2M in THF, 6 mmol). The mixture was stirred at RT for 14 h. An aqueous solution of NaHCO3 was added and the mixture was extracted three times with methylene chloride. The combined organic layers were washed with brine and dried over MgSO4. The solvent was removed by evaporation and the product was purified by reversed phase chromatography (C8) using acetonitrile and aqueous ammonium acetate solution (0.1 M) as eluent. There was obtained 0.20 g (59%) of 1-[1-(diphenylmethyl)azetidin-3-yl]-N,N-dimethylpiperidine-4-carboxamide. 1H NMR (500 MHz, CDCl3): δ 1.6-2.0 (cm, 6H), 2.4-2.5 (m, 1H), 2.8 (m, 2H), 2.9-3.0 (m, 5H), 3.1 (s, 3H), 3.4 (t, 2H), 4.4 (s, 1H), 7.2 (t, 2H), 7.3 (t, 4H), 7.4 (d, 4H); LCMS: m/z 378 (M+1)+.

후처리

  1. extractionthe mixture was extracted three times with methylene chloride
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed by evaporation
  5. customthe product was purified by reversed phase chromatography (C8)

출처 및 근거

ORD 기록
ord-f39b68eac6394999876f91dca8a54946
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106208B2

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