Ammonia → HCID 90312643, compound

HRID 1523758Notes

Reaction equation

HRID 1523758 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][S:5]([N:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)(=[O:7])=[O:6].Cl.CC[N:22]([CH2:25]C)CC.N.C1C[O:31]CC1>>[Br:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][S:5]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:25]([NH2:22])=[O:31])[CH2:10][CH2:9]1)(=[O:6])=[O:7]

Participants

6

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 90314014HCID 90314014, compound

Product 1

HCID 90312643HCID 90312643, compoundYield 69%

Procedure

To a mixture of 1-(2-bromobenzylsulfonyl)piperidin-4-amine.HCl (200 mg, 0.54 mmol) and Et3N (164 mg, 1.62 mmol) in dry THF (20 mL) was added (COCl2)3 (160 mg, 0.54 mmol) at rt. The reaction mixture was stirred at rt for 1 hour, and then a solution of NH3 in THF (4 N, 10 mL) was added drop-wise. The resulting mixture was stirred at rt for 5 hours, concentrated to dryness and purified by HPLC to give the title compound (140 mg, 69%). MS (ESI): mass calcd. for C13H18BrN3O3S, 375.03; m/z found, 376.0 [M+H]+.

Workup

  1. stirringThe resulting mixture was stirred at rt for 5 hours
  2. concentrationconcentrated to dryness
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-b01b52bcb7854b65bb2f83ff49922717
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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