Ammonia → HCID 18426289, compound

HRID 1280988Notes

Reaction equation

HRID 1280988 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:11]1[CH:28]=[CH:27][C:14]([CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([NH:22][C:23](=[O:26])[CH2:24][NH2:25])[CH2:18][CH2:17]2)=[CH:13][CH:12]=1.C(N(CC)CC)C.N>C(Cl)(Cl)Cl>[C:1]([NH:25][CH2:24][C:23]([NH:22][CH:19]1[CH2:18][CH2:17][N:16]([CH2:15][C:14]2[CH:13]=[CH:12][CH:11]=[CH:28][CH:27]=2)[CH2:21][CH2:20]1)=[O:26])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 18426167HCID 18426167, compound

Product 1

HCID 18426289HCID 18426289, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of benzoyl chloride (0.060 mmol) in chloroform (0.4 mL) was added to a solution of 1-(4-chlorobenzyl)-4-(glycylamino)piperidine (0.050 mmol) and triethylamine (0.070 mmol) in chloroform (1.0 mL). After the reaction mixture was agitated at room temperature for 2.5 h, (aminomethyl)polystyrene resin (1.04 mmol/g, 50 mg, 50 mmol) was added and the mixture was agitated at room temperature for 12 h. The reaction mixture was filtered and the resin was washed with dichloromethane (0.5 mL). The filtrate and washing were combined, dichloromethane (4 mL) was added, and the solution was washed with 2 N aqueous NaOH solution (0.5 mL) to give 4-(N-benzoylglycyl)amino-1-benzylpiperidine (compound No. 386) (11.3 mg, 64%): The purity was determined by RPLC/MS (94%); ESI/MS m/e 352.0 (M++H, C21H25N3O2).

Workup

  1. stirringthe mixture was agitated at room temperature for 12 h
  2. filtrationThe reaction mixture was filtered
  3. washthe resin was washed with dichloromethane (0.5 mL)
  4. washThe filtrate and washing
  5. additiondichloromethane (4 mL) was added
  6. washthe solution was washed with 2 N aqueous NaOH solution (0.5 mL)

Sources & evidence

ORD record
ord-e772b5e8f295444fb7c9159020d82656
Source dataset
uspto-grants-2002_09
Patent number
US06451842B1

Reaction notes

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