Hydrogen Bromide → 3-amino-5-cycloheptyl-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one

HRID 743699Notes

Reaction equation

HRID 743699 reaction equation
C(OC([NH:11][CH:12]1[N:18]=[C:17]([CH:19]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[C:16]2[CH:26]=[CH:27][CH:28]=[CH:29][C:15]=2[N:14]([CH3:30])[C:13]1=[O:31])=O)C1C=CC=CC=1.Br.C(OCC)C>CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O>[NH2:11][CH:12]1[N:18]=[C:17]([CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)[C:16]2[CH:26]=[CH:27][CH:28]=[CH:29][C:15]=2[N:14]([CH3:30])[C:13]1=[O:31]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 214804783(R,S)-[(Benzyloxycarbonyl)amino]-5-cycloheptyl-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one

Product 1

HCID 214804643-amino-5-cycloheptyl-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one

Reagents, catalysts & solvents 1

HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterSolvent

Procedure

3(R,S)-[(Benzyloxycarbonyl)amino]-5-cycloheptyl-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one (435 mg) was treated with a solution of 30% hydrogen bromide in glacial acetic add (10 ml) and stirred for 20 min at room temperature. The mixture was then added dropwise onto cold (0° C.) diethyl ether (50 ml). A white solid precipitated which was filtered off. The solid was treated with 10% sodium hydroxide solution (50 ml), then extracted with ethyl acetate (80 ml). The organic layer was separated, dried (Na2SO4) and evaporated to give crude 3(R,S)-amino-5-cycloheptyl-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one as a colourless oil.

Workup

  1. additionadd (10 ml)
  2. customA white solid precipitated which
  3. filtrationwas filtered off
  4. additionThe solid was treated with 10% sodium hydroxide solution (50 ml)
  5. extractionextracted with ethyl acetate (80 ml)
  6. customThe organic layer was separated
  7. dry with materialdried (Na2SO4)
  8. customevaporated

Sources & evidence

ORD record
ord-904098f8f4964111ae5f163e4a47d59a
Source dataset
uspto-grants-1996_09
Patent number
US05556969

Reaction notes

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