Acetic Acid → HCID 871814, compound

HRID 2094917Notes

Reaction equation

HRID 2094917 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH2:10])=[CH:5][CH:4]=1.C(O)(=O)C.[F:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=1[F:24])[CH:19]=O.C([BH3-])#N>ClCCl>[F:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=1[F:24])[CH2:19][NH:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 754524-MethoxybenzylamineHCID 498716Cyano-borohydrideHCID 5880883,4-Difluorobenzaldehyde

Product 1

HCID 871814HCID 871814, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

To (4-methoxyphenyl)methanamine (1.77 mL, 13.6 mmol) and acetic acid (2.7 mL, 45 mmol) in dichloromethane (15 mL) was added 3,4-difluorobenzaldehyde (1.0 m, 9.08 mmol). This mixture was heated in the microwave at 100° C. for 15 min. The reaction was cooled to room temperature and macroporous cyanoborohydride resin (9.8 g, 22.7 mmol) was added in portions. This mixture was stirred at room temperature for 16 hours. The resin was filtered off and rinsed with dichloromethane and the organics were washed with saturated sodium bicarbonate until bubbling ceased. The organics were dried over sodium sulfate and concentrated via rotovap. The resulting crude material was purified by silica gel chromatography using methanol dichloromethane gradient as eluent to afford N-(3,4-difluorobenzyl)(4-methoxyphenyl)methanamine as a yellowish oil (1.9 g, 80% yield). MS (M+H, 264); 1H NMR (400 MHz, DMSO-d6): δ, ppm: 2.63 (br s, 1H), 3.56 (s, 2H), 3.61 (s, 2H), 3.71 (s, 3H), 6.84 (d, J=8.8 Hz, 2H), 7.14 (m, 1H), 7.21 (d, J=8.4 Hz, 2H), 7.34 (m, 2H).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationThe resin was filtered off
  3. washrinsed with dichloromethane
  4. washthe organics were washed with saturated sodium bicarbonate
  5. customuntil bubbling
  6. dry with materialThe organics were dried over sodium sulfate
  7. concentrationconcentrated via rotovap
  8. customThe resulting crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-ccb34cd3056841ae9a17b4890f7b2413
Source dataset
uspto-grants-2013_05
Patent number
US08445692B2

Reaction notes

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