4-Nitrophenyl chloroformate → HCID 68891845, compound

HRID 657252Notes

Reaction equation

HRID 657252 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:13][C:14]([O:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1)=[O:15]>C1COCC1>[ClH:13].[N+:23]([C:20]1[CH:19]=[CH:18][C:17]([O:16][C:14](=[O:15])[NH:12][C:9]2[CH:10]=[CH:11][C:6]([N:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)=[CH:7][CH:8]=2)=[CH:22][CH:21]=1)([O-:25])=[O:24]

Participants

4

Reactant 2

HCID 821294-Nitrophenyl chloroformateHCID 8088414-(Pyrrolidin-1-yl)aniline

Product 1

HCID 68891845HCID 68891845, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 4.9 g (30.4 mmol) of 4-pyrrolidin-1-yl-phenylamine in 70 mL of anhydrous THF at room temperature, was added dropwise a solution of 6.4 g (32 mmol) of 4-nitrophenyl chloroformate in 16 mL of anhydrous THF. After the addition was complete, the mixture was stirred for 1 h and then filtered. The precipitate was washed first with anhydrous THF (2×10 mL) and then with anhydrous DCM (3×10 mL) and dried in vacuo to yield 10 g of an off-white solid. 1H-NMR (300 MHz, CD3OD): 10.39 (s, 1H), 8.32 (d, 2H), 7.73 (d, 2H), 7.60 (d, 2H), 7.48 (d, 2H), 3.86-3.68 (bs, 4H), 2.35-2.24 (bs, 4H). LC/MS (ESI): 328 (MH)+.

Workup

  1. additionAfter the addition
  2. filtrationfiltered
  3. washThe precipitate was washed first with anhydrous THF (2×10 mL)
  4. dry with materialwith anhydrous DCM (3×10 mL) and dried in vacuo

Sources & evidence

ORD record
ord-884ec7b661c741679205b88ea8e1ea29
Source dataset
uspto-grants-2011_12
Patent number
US08071768B2

Reaction notes

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