Triethylamine → 5-(1-(biphenyl-4-ylmethyl)piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one

HRID 1397896노트

반응식

HRID 1397896 반응식
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:16]=[CH:15][C:10]3[NH:11][C:12](=[O:14])[NH:13][C:9]=3[CH:8]=2)[CH2:3][CH2:2]1.[C:17]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:22]=[CH:21][C:20]([CH:23]=O)=[CH:19][CH:18]=1.CCN(CC)CC.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>CS(C)=O.C(OCC)(=O)C>[C:17]1([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:18]=[CH:19][C:20]([CH2:23][N:1]2[CH2:2][CH2:3][CH:4]([C:7]3[CH:16]=[CH:15][C:10]4[NH:11][C:12](=[O:14])[NH:13][C:9]=4[CH:8]=3)[CH2:5][CH2:6]2)=[CH:21][CH:22]=1

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 76689(1,1'-Biphenyl)-4-carboxaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 824933395-(Piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one

생성물 1

HCID 870562765-(1-(biphenyl-4-ylmethyl)piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one수율 51%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

실험 절차

A representative procedure for the synthesis of the piperidinyl aldehydes is the following. To a solution of compound 5 (0.15 g, 0.45 mmol) and biphenyl-4-carbaldehyde a (0.1 g, 0.55 mmol) in DMSO (2 mL) at 0° C. was added Et3N (0.13 mL, 0.97 mmol). After being stirred for 0.5 h at room temperature, NaBH(OAc)3 (0.11 g, 0.53 mmol) was added, and the mixture was stirred for 6 h. To the reaction mixture was added sat. NaHCO3 solution (10 mL), and the mixture was stirred for 15 min, followed by the addition of ethyl acetate (30 mL). The organic layer was separated and washed with sat. NaHCO3 and brine, and dried over Na2SO4 and evaporated. The light yellow solid was crystallized from diethyl ether to obtain the title compound 5a. Yield: 51%, off-white solid, mp>260° C. IR (KBr, cm−1) 3429 (CONH), 3055 (Ar—H), 2966 (Alph-H), 1703 (CO), 1620, 1518, 1422 (C—C), 1226 (C—N), 1145 (C-0); 1H NMR (500 MHz, DMSO d6) δ 1.62-1.71 (m, 4H, 2CH2), 2.04 (m, 2H, CH2), 2.48 (m, 1H, CH), 2.92 (m, 2H, CH2), 3.51 (s, 2H, NCH2), 6.77-6.81 (m, 3H, 3Ar—H), 7.32 (m, 1H, Ar—H), 7.40-7.45 (m, 4H, 4Ar—H), 7.59-7.64 (m, 4H, 4Ar—H), 10.43 (br. s, 1H, NH), 10.48 (br. s, 1H, NH), 13C NMR (125.7 MHz, DMSO d6) δ 33.64 (CH2), 41.86 (CH), 53.66 (CH2), 59.45 (NCH2), 106.91 (Ar—C), 108.42 (Ar—C), 118.99 (Ar—C), 126.56 (Ar—C), 126.66 (Ar—C), 127.42 (Ar—C), 127.98 (Ar—C), 129.03 (Ar—C), 129.06 (Ar—C), 129.63 (Ar—C), 138.92 (Ar—C), 140.11 (Ar—C), 155.59 (C═O). Anal. Calcd for C25H25N3O: C, 78.30; H, 6.57; N, 10.96%. Found: C, 78.22; H, 6.63; N, 10.86%.

후처리

  1. stirringthe mixture was stirred for 6 h
  2. stirringthe mixture was stirred for 15 min
  3. customThe organic layer was separated
  4. washwashed with sat. NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe light yellow solid was crystallized from diethyl ether

출처 및 근거

ORD 기록
ord-81482e04c45141f1becdd86e2c886c7c
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901304B1

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