Hydrochloric Acid → HCID 19069264, compound

HRID 1957345Notes

Reaction equation

HRID 1957345 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH2:10]([NH2:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl.[BH3-]C#N.[Na+]>ClCl.CO.C(O)(=O)C>[ClH:1].[CH2:10]([NH:17][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 313Hydrochloric Acid2×HCID 7504BenzylamineHCID 77264-ChlorobenzaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 19069264HCID 19069264, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 24526ChlorineSolvent

Procedure

To 4-chlorobenzaldehyde (1.5 g, 10.7 mmol) dissolved in 40 mL CH2 Cl2 was added benzylamine (1.15g, 10.7 mmol) followed by 1 mL of 6N HCl. The resulting cloudy solution was stirred overnight at room temperature and then concentrated in vacuo to give a white solid. The solid was immediately dissolved in 50 mL of MeOH and the pH of the solution was adjusted to 6 with glacial acetic acid. To this solution was added NaCNBH3 (0.67 g, 10.7 mol), and the resulting clear solution was stirred three hours at room temperature. The mixture was acidified to pH 2 with 6M HCl whereupon a thick white slurry developed. The solid was stirred for 30 minutes and filtered, yielding the title compound as a white solid. 1H NMR δ(DMSO-d6, 300 MHz) δ4.1-4.2 (broad multiplet, 4H), 7.4-7.6 (m, 9H). MS (DCl/NH3) m/e 232 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. customto give a white solid
  3. stirringthe resulting clear solution was stirred three hours at room temperature
  4. stirringThe solid was stirred for 30 minutes
  5. filtrationfiltered

Sources & evidence

ORD record
ord-5c41679d1f3341c3950ba3ef4d587268
Source dataset
uspto-grants-1998_07
Patent number
US05783593

Reaction notes

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