Allylamine → (S,Z)-3-Amino-1-benzyl-3,4-dihydro-1H-azepin-2(7H)-one

Reaction equation

[NH2:1][C@H:2]1[CH2:9][CH:8]=[CH:7][CH2:6]C[N:4]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:3]1=[O:17].C(N)C=C>>[NH2:1][C@H:2]1[CH2:9][CH:8]=[CH:7][CH2:6][N:4]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:3]1=[O:17]

Participants

Reactant 2

HCID 7853Allylamine

HCID 68292242(S,Z)-3-amino-1-benzyl-3,4,7,8-tetrahydroazocin-2(1H)-one

Product 1

HCID 68292696(S,Z)-3-Amino-1-benzyl-3,4-dihydro-1H-azepin-2(7H)-one

Procedure

(S,Z)-3-Amino-1-benzyl-3,4-dihydro-1H-azepin-2(7H)-one (6.15 mg, 0.028 mmol) was synthesized as described for the preparation of Intermediate 44 using prop-2-en-1-amine in step A. Anal. Calcd. for C13H16N2O m/z 216.2. found: 217.0 (M+H)+.

Sources & evidence

ORD record: ord-9d27a4fc0eaa4534824af22e107eed24
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346852B2

Reaction notes

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