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Salicylaldehyde → n-(2-Hydroxyphenylmethyl)-n'-(1h-benzimidazol-2-ylmethyl)-n'-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

HRID 7149
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인쇄 미리보기

반응식

HRID 7149 반응식
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]([CH:21]1[C:30]2[N:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH2:24][CH2:23][CH2:22]1)[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][NH2:20])=[CH:15][CH:14]=1.[CH:31](=O)[C:32]1[C:33](=[CH:35][CH:36]=[CH:37][CH:38]=1)[OH:34].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[OH:34][C:33]1[CH:35]=[CH:36][CH:37]=[CH:38][C:32]=1[CH2:31][NH:20][CH2:19][C:16]1[CH:15]=[CH:14][C:13]([CH2:12][N:11]([CH2:10][C:2]2[NH:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:1]=2)[CH:21]2[C:30]3[N:29]=[CH:28][CH:27]=[CH:26][C:25]=3[CH2:24][CH2:23][CH2:22]2)=[CH:18][CH:17]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6998SalicylaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 21985008N-[(1H-Benzo[d]imidazol-2-yl)methyl]-N-(4-(aminomethyl)-benzyl)-5,6,7,8-tetrahydroquinolin-8-amine

생성물 1

HCID 22018567n-(2-Hydroxyphenylmethyl)-n'-(1h-benzimidazol-2-ylmethyl)-n'-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine수율 54%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

Using General Procedure B: To a stirred solution of N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (147 mg, 0.37 mmol) and salicylaldehyde (0.04 mL, 0.38 mmol) in CH2Cl2 (5 mL) was added NaBH(OAc)3 (100 mg, 0.47 mmol) and the resultant mixture was stirred at room temperature for 16 hours. Purification of the crude material by radial chromatography on silica gel gel (2 mm plate, 75:1:1 CH2Cl2/MeOH/NH4OH) afforded the free amine (100 mg, 54%) as a white foam.

후처리

  1. customPurification of the crude material by radial chromatography on silica gel gel (2 mm plate, 75:1:1 CH2Cl2/MeOH/NH4OH)

출처 및 근거

ORD 기록
ord-f5d0730dc5f14fbd876c5c487555fef6
출처 데이터셋
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07084155B2

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