Benzoic acid, 4-fluoro-, ethyl ester → 4-Benzylbenzoate piperidine 4-ethyl benzoate

HRID 2190555ノート

反応式

HRID 2190555 の反応式
[CH2:1]([O:8][C:9](=[O:22])[C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:21][CH2:20]NCC2)=[CH:12][CH:11]=1)[C:2]1C=CC=CC=1.C([O:25][C:26](=[O:34])[C:27]1[CH:32]=[CH:31][C:30](F)=[CH:29][CH:28]=1)C.C(N(C(C)C)CC)(C)C>CN(C1C=CN=CC=1)C.CS(C)=O>[CH2:26]([C:13]1[CH:12]=[CH:11][C:10]([C:9]([O-:8])=[O:22])=[CH:15][CH:14]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[NH:16]1[CH2:13][CH2:14][CH2:15][CH2:20][CH2:21]1.[CH3:1][CH2:2][C:30]1[CH:29]=[CH:28][C:27]([C:26]([OH:25])=[O:34])=[CH:32][CH:31]=1

参加物

6

反応物 3

HCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 81531DiisopropylethylamineHCID 539216634-Piperazin-1-yl-benzoic acid benzyl ester

生成物 1

HCID 1317300884-Benzylbenzoate piperidine 4-ethyl benzoate収率 128%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 679Dimethyl Sulfoxide溶媒

実験手順

A mixture of 4-piperazin-1-yl-benzoic acid benzyl ester (500 mg, 1.68 mmol), 4-fluoro benzoic acid ethyl ester (1.4 g, 8.4 mmol), diisopropylethyl amine (1.47 mL, 8.4 mmol) and a catalytic amount of DMAP in DMSO (6 mL) was stirred at 130° C. in a sealed tube for 70 h. The mixture was the cooled partitioned between EtOAc and water. The EtOAc layer was collected, dried over Na2SO4, filtered and concentrated. The residue was suspended in hexanes and the suspension was then filtered. The solid obtained passed through a plug of silica gel using 0-100% EtOAc in hexanes to afford the product (480 mg, Yield; 64%). HRMS m/z calcd for C27H28N2O4 [M+H]+: 445.2122; Found: 445.2120.

後処理

  1. custompartitioned between EtOAc and water
  2. customThe EtOAc layer was collected
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. filtrationthe suspension was then filtered
  7. customThe solid obtained

出典と根拠

ORDレコード
ord-965bb96018b546ef8eeba852a2b0688a
出典データセット
uspto-grants-2012_12
特許番号
US08324385B2

反応ノート

読み込み中…