Phenyl chloroformate → HCID 59807140, compound

HRID 1922419Notes

Reaction equation

HRID 1922419 reaction equation
[CH3:1][N:2](C)[CH2:3][CH2:4][N:5]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]2[CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=[CH:15][C:6]1=2.[C:20]1([O:26][C:27](Cl)=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)Cl>[CH3:1][N:2]([CH2:3][CH2:4][N:5]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]2[CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=[CH:15][C:6]1=2)[C:27](=[O:28])[O:26][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 15891Phenyl chloroformateHCID 59807142HCID 59807142, compound

Product 1

HCID 59807140HCID 59807140, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of N,N-dimethyl-2-(7-nitro-2,3,4,5-tetrahydro-1H-benzo[b]azepin-1-yl)ethanamine (400 mg, 1.52 mmol) in 10 mL CH2Cl2 was treated dropwise with phenylchloroformate (286 μL, 2.28 mmol). The reaction was stirred at room temperature for 21 hours then partitioned between CH2Cl2 (100 mL) and 1N NaOH (20 mL). After extraction, the organic layer was separated and the aqueous layer was extracted with additional CH2Cl2 (50 mL). The combined organic layer was dried over Na2SO4, filtered and concentrated to give a yellow residue. This residue was subjected to flash chromatography on silica gel using CH2Cl2 to give a yellow residue (460 mg, 82.0%). 1H-NMR (CDCl3) δ 7.99 (dd, J=2.7, 9.0 Hz, 1H), 7.93 (d, J=2.7 Hz, 1H), 7.40-7.34 (m, 2H), 7.23-7.18 (m, 1H), 7.10-7.04 (m, 2H), 6.87 (dd, J=6.3, 2.7 Hz, 1H), 3.65-3.55 (m, 4H), 3.39-3.31 (m, 2H), 3.11 and 3.05 (2×s, 3H), 2.88-2.85 (m, 2H), 1.85-1.65 (m, 4H). MS (ESI): 370.2 (M+1).

Workup

  1. customthen partitioned between CH2Cl2 (100 mL) and 1N NaOH (20 mL)
  2. extractionAfter extraction
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was extracted with additional CH2Cl2 (50 mL)
  5. dry with materialThe combined organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a yellow residue

Sources & evidence

ORD record
ord-c5730b3967fa47b08265f2bda6319dec
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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