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Formaldehyde → N,N-Dimethyl-2-(2-(1-methyl-1H-imidazol-4-ylsulfonyl)-1,2,3,4-tetrahydroisoquinolin-7-yl)-3-phenylpropan-1-amine

HRID 2167445
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HRID 2167445 반응식
[CH3:1][N:2]1[CH:6]=[C:5]([S:7]([N:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][C:14]([CH:20]([CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH2:21]N)=[CH:15][CH:16]=3)[CH2:11]2)(=[O:9])=[O:8])[N:4]=[CH:3]1.[CH2:30]=O.[B-][C:33]#[N:34].[Na+].O>CO>[CH3:30][N:34]([CH3:33])[CH2:21][CH:20]([C:14]1[CH:13]=[C:12]2[C:17]([CH2:18][CH2:19][N:10]([S:7]([C:5]3[N:4]=[CH:3][N:2]([CH3:1])[CH:6]=3)(=[O:9])=[O:8])[CH2:11]2)=[CH:16][CH:15]=1)[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1
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참가 물질

6

반응물 4

HCID 712FormaldehydeHCID 962WaterHCID 20587905Sodium cyanoborohydride [MI]HCID 566426142-(2-(1-Methyl-1H-imidazol-4-ylsulfonyl)-1,2,3,4-tetrahydroisoquinolin-7-yl)-3-phenylpropan-1-amine

생성물 1

HCID 56847394N,N-Dimethyl-2-(2-(1-methyl-1H-imidazol-4-ylsulfonyl)-1,2,3,4-tetrahydroisoquinolin-7-yl)-3-phenylpropan-1-amine수율 18.1%

시약·촉매·용매

1
HCID 887Methanol용매

실험 절차

0.058 mmol of 2-(2-(1-methyl-1H-imidazol-4-ylsulfonyl)-1,2,3,4-tetrahydroisoquinolin-7-yl)-3-phenylpropan-1-amine (example 1) were dissolved in 2 ml of methanol. A solution of formaldehyde (0.351 mmol, 37%) and 0.351 mmol of sodium cyanotrihydroborate were added and the mixture was stirred at room temperature over night. H2O was added to the reaction mixture and the aqueous phase was extracted with CH2Cl2. The combined organic phases were dried over MgSO4 and filtered. The filtrate was concentrated to 6 mg of crude solid material. The solid was washed with diisopropyl ether and dissolved in methanol. An equimolar amount of 1 N HCl was added and the volatiles removed in vacuo. The residue was washed with diethyl ether, dissolved in H2O, acidified with 1 N HCl and washed with additional diethyl ether. The aqueous phase was freeze dried to give 4.6 mg of the desired product (16.5%).

후처리

  1. extractionthe aqueous phase was extracted with CH2Cl2
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated to 6 mg of crude solid material
  5. washThe solid was washed with diisopropyl ether
  6. dissolutiondissolved in methanol
  7. additionAn equimolar amount of 1 N HCl was added
  8. customthe volatiles removed in vacuo
  9. washThe residue was washed with diethyl ether
  10. dissolutiondissolved in H2O
  11. washwashed with additional diethyl ether
  12. customdried

출처 및 근거

ORD 기록
ord-94c91fdd92fe4e9cb06f2171294602ef
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09045459B2

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