Benzylamine → HCID 23298428, compound

HRID 2393559Notes

Reaction equation

HRID 2393559 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][C:11]2=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([BH3-])#N.[Na+]>C(O)C.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][CH:11]2[NH:22][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 7504BenzylamineHCID 384457-Nitro-1-tetraloneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 23298428HCID 23298428, compound

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 702EthanolSolvent

Procedure

7-Nitro-1-tetralone (2.0 g, 10.5 mmol), benzylamine (1.2 ml, 10.5 mmol) and titanium isopropoxide (3.9 ml, 13.1 mmol) were combined and stirred for 1 hr. The mixture was diluted with absolute ethanol (12 ml), treated with sodium cyanoborohydride (0.44 g, 7.0 mmol) and allowed to stir for 20 hr. The solids were filtered and washed with ethanol. The ethanol was concentrated and the remaining oil used immediately in the next reaction: M.S. (M+H)+ =283.

Workup

  1. stirringto stir for 20 hr
  2. filtrationThe solids were filtered
  3. washwashed with ethanol
  4. concentrationThe ethanol was concentrated
  5. customthe remaining oil used immediately in the next reaction

Sources & evidence

ORD record
ord-e3ec712378254e46ab95d03371f5aab8
Source dataset
uspto-grants-1998_09
Patent number
US05807886

Reaction notes

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