Triethylamine → HCID 2435435, compound

HRID 1782706Notes

Reaction equation

HRID 1782706 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11])([O-:3])=[O:2].[NH2:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:17][CH2:16]1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:17][CH2:16]1)(=[O:12])=[O:11])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 4158521-Benzyl-4-piperidylamine

Product 1

HCID 2435435HCID 2435435, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Whilst carrying out external cooling with ice water a solution of 44.3 g (0.2 mol) of 2-nitrobenzenesulphonyl chloride in 250 ml of chloroform was added dropwise to a solution of 38.0 g (0.2 mol) of 4-amino-1-(phenylmethyl)piperidine and 22.0 g (0.22 mol) of triethylamine in 250 ml of chloroform. After the cooling was stopped the mixture was stirred for a further 30 minutes at room temperature, the reaction mixture was then extracted twice with 1 l water. The aqueous extracts were extracted once more with 100 ml of dichloromethane, the combined organic phases were then dried over sodium sulphate and evaporated down in vacuo. The highly viscous light-brown substance obtained in a yield of 75.0 g (99.9% of theory) was further processed without any more purification.

Workup

  1. extractionthe reaction mixture was then extracted twice with 1 l water
  2. extractionThe aqueous extracts were extracted once more with 100 ml of dichloromethane
  3. dry with materialthe combined organic phases were then dried over sodium sulphate
  4. customevaporated down in vacuo
  5. customThe highly viscous light-brown substance obtained in a yield of 75.0 g (99.9% of theory)
  6. customwas further processed without any more purification

Sources & evidence

ORD record
ord-fa4bb05d0c4c4347bdb647373b5eaf41
Source dataset
uspto-grants-2009_03
Patent number
US07498325B2

Reaction notes

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