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

HRID 369764

반응식

HRID 369764 반응식
[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

참가 물질

8

반응물 5

HCID 240Benzaldehyde2회HCID 65853EltoprazineHCID 4311764Sodium borohydride2회HCID 150064211-(3-Chloropropyl)imidazolidin-2-oneHCID 232826641-[3-[4-(1,4-Benzodioxan-5-yl)-1-piperazinyl]-1-propyl]-2-imidazolidinone

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 22328969EtOH ethyl acetate triethylamine용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-6ff11964173745ec931ced3cb706d291
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06140331

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