Acetic Acid → HCID 53392446, compound

HRID 1922415Notes

Reaction equation

HRID 1922415 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH:12]1[CH2:16][CH2:15][NH:14][CH2:13]1)[CH2:7][CH2:6][CH2:5]2.C=O.[C:19](O)(=O)C.C([BH3-])#N.[Na+]>CO.CO.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH:12]1[CH2:16][CH2:15][N:14]([CH3:19])[CH2:13]1)[CH2:7][CH2:6][CH2:5]2

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 53392538HCID 53392538, compound

Product 1

HCID 53392446HCID 53392446, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of 6-bromo-1-(pyrrolidin-3-yl)-1,2,3,4-tetrahydroquinoline (200 mg, 0.71 mmol) in 7 mL anhydrous methanol was treated with formaldehyde (37% aqueous solution, 79 μL, 1.07 mmol) followed by acetic acid (100 μL, 1.78 mmol). The solution was treated with sodium cyanoborohydride (67 mg, 1.07 mmol). The suspension was stirred at room temperature for 3 hours. The mixture was concentrated to dryness and partitioned between 20 mL 1N NaOH and 100 mL of CH2Cl2. After extraction, the organic layer was dried over Na2SO4, filtered and concentrated to give an oily residue which was subjected to flash chromatography on silica gel using 5% 2M NH3 in MeOH/CH2Cl2. A yellow oil was obtained (153 mg, 72.9%). 1H-NMR (CDCl3) δ 7.10 (dd, J=2.4, 8.7 Hz, 1H), 7.04 (d, J=2.4 Hz, 1H), 6.57 (d, J=9.0 Hz, 1H), 4.47-4.38 (m, 1H), 3.26 (t, J=5.7 Hz, 2H), 2.81-2.68 (m, 4H), 2.60-2.55 (m, 1H), 2.40-2.24 (m, 1H), 2.35 (s, 3H), 2.24-2.13 (m, 1H), 1.92-1.79 (m, 3H). MS(ESI): 295.1 and 297.1 (M+1).

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. custompartitioned between 20 mL 1N NaOH and 100 mL of CH2Cl2
  3. extractionAfter extraction
  4. dry with materialthe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an oily residue which
  8. customA yellow oil was obtained (153 mg, 72.9%)

Sources & evidence

ORD record
ord-4c35de0dbd2042f8bb57dcc48b3f442c
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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