Hexahydro-1,4-diazepine → 1-(2,3-Dihydro-6-methoxy-1H-inden-1-yl)hexahydro-1H-1,4-diazepine

HRID 1956146Notes

Reaction equation

HRID 1956146 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:8][O:9][C:10]1[CH:18]=[C:17]2[C:13]([CH2:14][CH2:15][C:16]2=O)=[CH:12][CH:11]=1.[BH4-].[Na+]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH3:8][O:9][C:10]1[CH:18]=[C:17]2[C:13]([CH2:14][CH2:15][CH:16]2[N:1]2[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 68163Hexahydro-1,4-diazepineHCID 3340366-Methoxy-1-IndanoneHCID 4311764Sodium borohydride

Product 1

HCID 223753641-(2,3-Dihydro-6-methoxy-1H-inden-1-yl)hexahydro-1H-1,4-diazepineYield 70.5%

Reagents, catalysts & solvents 1

HCID 11026Titanium isopropoxideCatalyst

Procedure

Homopiperazine (30.6 g, 0.306 mol), 6-methoxy-indan-1-one (4.95 g, 30.56 mmol), titanium(IV) isopropoxide (17.9 ml, 60 mmol) and sodium borohydride (2.7 g, 71 mmol) were reacted by Method A to give the product (5.3 g, 70.5%). The crude product was used without purification.

Sources & evidence

ORD record
ord-656b01bc73b24df498b317a5a8b9d510
Source dataset
uspto-grants-1998_07
Patent number
US05780470

Reaction notes

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