Benzylamine → HCID 23600674, compound

HRID 892265Notes

Reaction equation

HRID 892265 reaction equation
F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[CH2:28]([NH2:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[CH2:36]([O:43][C:44]([N:46]1[CH2:51][CH2:50][C:49]([CH2:58][C:59](O)=[O:60])([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[CH2:48][CH2:47]1)=[O:45])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(N(CC)CC)C>O1CCCC1.C(OCC)C>[CH2:36]([O:43][C:44]([N:46]1[CH2:51][CH2:50][C:49]([CH2:58][C:59](=[O:60])[NH:35][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[CH2:48][CH2:47]1)=[O:45])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 23600420HCID 23600420, compound

Product 1

HCID 23600674HCID 23600674, compoundYield 90.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (0.120 g, 0.271 mmol) was added to a solution of benzyl amine (0.030 mL, 0.271 mmol), 4-carboxymethyl-4-phenyl-piperidine-1-carboxylic acid benzyl ester (0.100 g, 0.247 mmol), triethylamine (0.103 mL, 0.741 mmol) in tetrahydrofuran (5 mL). After 1 hour the mixture was diluted with ethyl ether (20 mL), washed with saturated aqueous sodium bicarbonate (20 mL) followed by water (2×10 mL). Organic layer collected, concentrated under reduced pressure and crude product purified by column chromatography to give 0.099 g of 4-(benzylcarbamoyl-methyl)-4-phenyl-piperidine-1-carboxylic acid benzyl ester. LRMS m/z 443.2 (M+H)+.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate (20 mL)
  2. customOrganic layer collected
  3. concentrationconcentrated under reduced pressure and crude product
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-bd7f1432dbac420882a199c06f2cfd8d
Source dataset
uspto-grants-2006_02
Patent number
US07005436B2

Reaction notes

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