Phosgene → HCID 86615684, compound

HRID 644348Notes

Reaction equation

HRID 644348 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].[NH:5]1[CH2:10][CH2:9][CH:8]([N:11]2[CH2:17][CH2:16][C:15]3[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=3[NH:13][C:12]2=[O:22])[CH2:7][CH2:6]1.C(N(C(C)C)C(C)C)C>C(Cl)Cl>[O:22]=[C:12]1[N:11]([CH:8]2[CH2:9][CH2:10][N:5]([C:1]([Cl:4])=[O:2])[CH2:6][CH2:7]2)[CH2:17][CH2:16][C:15]2[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=2[NH:13]1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 81531DiisopropylethylamineHCID 113795873-(Piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-one

Product 1

HCID 86615684HCID 86615684, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

6 g (12.1 mmol) phosgene (20 percent by weight in toluene) were added to a solution of 2.5 g (10.2 mmol) 3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one and 2.6 mL (14.9 mmol) ethyldiisopropylamine in 75 mL DCM cooled to 0° C. and the reaction mixture was stirred for 30 min at this temperature. It was allowed to come up to RT, evaporated down i.vac. to approx. 50 mL and filtered through silica gel, this washed with 200 mL DCM/EtOAc (1:1) and the combined filtrates were again evaporated down i.vac. The residue was stirred with diisopropylether, suction filtered and dried i.vac.

Workup

  1. customto come up to RT
  2. customevaporated down i.vac
  3. filtrationto approx. 50 mL and filtered through silica gel
  4. washthis washed with 200 mL DCM/EtOAc (1:1)
  5. customthe combined filtrates were again evaporated down i.vac
  6. stirringThe residue was stirred with diisopropylether, suction
  7. filtrationfiltered
  8. customdried i.vac

Sources & evidence

ORD record
ord-cc09fc9351c44f2d9c2ff6ec588f9b3d
Source dataset
uspto-grants-2010_04
Patent number
US07700589B2

Reaction notes

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