Benzylamine → HCID 43654054, compound

HRID 421973Notes

Reaction equation

HRID 421973 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.[Cl:16][CH2:17][CH2:18][CH2:19][S:20](Cl)(=[O:22])=[O:21]>C(Cl)Cl>[CH2:1]([NH:8][S:20]([CH2:19][CH2:18][CH2:17][Cl:16])(=[O:22])=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 8471TriethylamineHCID 154103-Chloropropanesulphonyl chloride

Product 1

HCID 43654054HCID 43654054, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Benzylamine (1 eq.) was dissolved in anhydrous DCM (0.5 M) and Et3N (1.1 eq.) was added; after cooling at 0° C., 1-chloro-3-propanesulfonyl chloride was slowly added and the mixture was stirred at RT for 20 h. All volatiles were evaporated in vacuo and the residue taken up with Et2O; the precipitate was filtered off and the filtrate was concentrated; addition of PE afforded N-benzyl-3-chloropropane-1-sulfonamide as a white solid (87%). (ES+) m/z 248 (M+H+). Di-tert-butyl dicarbonate (1.5 eq.) was slowly added to an ice-cooled 0.45 M THF solution of N-benzyl-3-chloropropane-1-sulfonamide. DMAP (0.1 eq.) was then added and the reaction stirred overnight at RT. All volatiles were removed in vacuo and the crude diluted with EtOAc, washed with HCl, sat. aq. NaHCO3 and brine. After drying over Na2SO4, all volatiles were evaporated in vacuo and the residual material used in the next step without purification. (ES+) m/z 348, 350 (M+H+).

Workup

  1. customAll volatiles were evaporated in vacuo
  2. filtrationthe precipitate was filtered off
  3. concentrationthe filtrate was concentrated
  4. additionaddition of PE

Sources & evidence

ORD record
ord-79ef6d403d0841db88b0fa4555121e5c
Source dataset
uspto-grants-2012_01
Patent number
US08101595B2

Reaction notes

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