Benzaldehyde → 1-[3-[4-(1,4-Benzodioxan-5-yl)-1-piperazinyl]-1-propyl]-3-benzyl-2-imidazolidinone, hydrochloride

HRID 369764

反応式

HRID 369764 の反応式
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([N:11]3[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][N:20]4[CH2:24][CH2:23][NH:22][C:21]4=[O:25])[CH2:13][CH2:12]3)[C:5]=2[O:4][CH2:3][CH2:2]1.O1C2C=CC=C(N3CCNCC3)C=2OCC1.[Cl:42]CCCN1CCNC1=O.[CH:52](=O)[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1.[BH4-].[Na+]>C(O)(=O)C.C(OCC)(=O)C.C(O)C.C(N(CC)CC)C>[ClH:42].[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([N:11]3[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][N:20]4[CH2:24][CH2:23][N:22]([CH2:52][C:53]5[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=5)[C:21]4=[O:25])[CH2:13][CH2:12]3)[C:5]=2[O:4][CH2:3][CH2:2]1

参加物

8

反応物 5

HCID 240Benzaldehyde2 回HCID 65853EltoprazineHCID 4311764Sodium borohydride2 回HCID 150064211-(3-Chloropropyl)imidazolidin-2-oneHCID 232826641-[3-[4-(1,4-Benzodioxan-5-yl)-1-piperazinyl]-1-propyl]-2-imidazolidinone

生成物 1

HCID 1317206581-[3-[4-(1,4-Benzodioxan-5-yl)-1-piperazinyl]-1-propyl]-3-benzyl-2-imidazolidinone, hydrochloride

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 22328969EtOH ethyl acetate triethylamine溶媒

実験手順

A solution of 1-[3-[4-(1,4-benzodioxan-5-yl)-1-piperazinyl]-1-propyl]-2-imidazolidinone (prepared from 1-(1,4-benzodioxan-5-yl)piperazin and 1-(3-chloro-1-propyl)-2-imidazolidinone by the method described in EXAMPLE 2) (2.5 g) and benzaldehyde (2.3 g) in glacial acetic acid (30 ml) was treated portionwise with sodium borohydride (0.6 g) keeping the temperature at 10° C. After stirring for 40 min. at room temperature additional benzaldehyde (2.3 g) and sodium borohydride (0.6 g) was added and the mixture stirred for 16 h at room temperature. Removal of solvent in vacuo gave a heavy oil which was applied to a silica gel column (eluent: ethyl acetate/ethanol/triethylamine=10:1:1). The title compound was isolated as a viscous oil which crystallized as the hydrochloride from an acetone/ether mixture by addition of an ether solution of dry HCl. Yield: 2.8 g, mp: 181-91° C. 1H NMR (δ, DMSO): 1.90-2.10 (m, 2H), 3.00-3.25 (m, 10H), 3.30 (t, 2H), 3.35-3.65 (m, 4H), 4.20 (s, 4H), 4.25 (s, 2H), 6.50 (d, 1H), 6.55 (d, 1H), 6.75 (t, 1H), 7.00 (b, 2H), 7.20-7.40 (m, 5H).

後処理

  1. customat 10° C
  2. additionwas added
  3. customRemoval of solvent in vacuo
  4. customgave a heavy oil which

出典と根拠

ORDレコード
ord-6ff11964173745ec931ced3cb706d291
出典データセット
uspto-grants-2000_10
特許番号
US06140331

関連ノート

読み込み中…