1-Amino-2-propanol → HCID 20562338, compound

HRID 1155109Notes

Reaction equation

HRID 1155109 reaction equation
ClC(Cl)C.[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[C:18]2[CH:19]=[C:20]([N:23]=[C:24]=[O:25])[CH:21]=[CH:22][C:17]=2[N:16]([CH3:26])[C:15](=[O:27])[CH2:14][N:13]=1.NC1C=CC2N(C)C(=O)CN=C(C3C=CC=CC=3F)C=2C=1.[NH2:49][CH2:50][CH:51]([OH:53])[CH3:52]>ClCCCl>[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[C:18]2[CH:19]=[C:20]([NH:23][C:24]([NH:49][CH2:50][CH:51]([OH:53])[CH3:52])=[O:25])[CH:21]=[CH:22][C:17]=2[N:16]([CH3:26])[C:15](=[O:27])[CH2:14][N:13]=1

Participants

6

Reactant 4

HCID 41-Amino-2-propanolHCID 63651,1-DichloroethaneHCID 922947-AminoflunitrazepamHCID 20562381HCID 20562381, compound

Product 1

HCID 20562338HCID 20562338, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A dichloroethane solution of [5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]isocyanate, prepared as described in paragraph (a) of Example 1 from 12.5 g (0.044 M) of 7-amino-5-(o-fluorophenyl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one, is added to a solution of 8 g of 1-amino-2-propanol in 100 ml of 1,2-dichloroethane, the mixture is stirred at room temperature for 15 minutes and then concentrated. The residue is purified on a 300 g silica gel column using methylene chloride and then acetone as the eluting agent. This operation is repeated once using ethyl acetate as the eluting agent. After crystallisation from ethyl acetate, there is obtained rac-1-[5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]-3-(2-hydroxypropyl)urea which melts at 149°-151° C. with decomposition.

Workup

  1. concentrationconcentrated
  2. customThe residue is purified on a 300 g silica gel column
  3. customAfter crystallisation from ethyl acetate

Sources & evidence

ORD record
ord-c783ee58a92e432ca9db7b8c96dee63f
Source dataset
uspto-grants-1981_11
Patent number
US04299767

Reaction notes

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