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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
Notes
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Reaction equation

HRID 2167445 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-94c91fdd92fe4e9cb06f2171294602ef
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09045459B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes