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

HRID 1397896ノート

反応式

HRID 1397896 の反応式
[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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-81482e04c45141f1becdd86e2c886c7c
出典データセット
uspto-grants-2014_12
特許番号
US08901304B1

反応ノート

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