Acetic Acid → HCID 59536329, compound

HRID 445265Notes

Reaction equation

HRID 445265 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][NH:10]2)=[CH:5][CH:4]=1.N1C=CC=CC=1.C(N(CC)CC)C.[O-:34][C:35]#[N:36].[K+].C(O)(=O)C>ClCCl>[F:20][C:2]([F:1])([F:19])[C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][N:10]2[C:35]([NH2:36])=[O:34])=[CH:7][CH:8]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 1049PyridineHCID 8471TriethylamineHCID 11378442Potassium cyanateHCID 166406961-(4-(Trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 59536329HCID 59536329, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (0.5 g, 2 mmol) (Example 9, step 3) in dichloromethane (10 mL) was treated with pyridine (1.4 mL, 17 mmol), triethylamine (0.5 mL, 4 mmol), potassium cyanate (0.3 g, 3 mmol), glacial acetic acid (1.00 mL, 17 mmol) and the resulting suspension was stirred at RT for 12 h. The reaction mixture was concentrated to a gummy residue which was taken up in dichloromethane (75 mL), washed with brine (35 mL), dried over anhydrous sodium sulfate, removed dichloromethane, and dried under high vacuum to yield (4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide as a white solid. MS (ESI pos. ion) m/z: 321 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated to a gummy residue which
  2. washwashed with brine (35 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customremoved dichloromethane
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-0c45b91acaad4fb1b02d317faee990ac
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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